CN106242941A - A kind of synthetic method of Cyclopropylmetyl bromide - Google Patents
A kind of synthetic method of Cyclopropylmetyl bromide Download PDFInfo
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- CN106242941A CN106242941A CN201610537776.6A CN201610537776A CN106242941A CN 106242941 A CN106242941 A CN 106242941A CN 201610537776 A CN201610537776 A CN 201610537776A CN 106242941 A CN106242941 A CN 106242941A
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- China
- Prior art keywords
- synthetic method
- bromating agent
- cyclopropylmetyl bromide
- cyclopropylmetyl
- carbinol
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- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000010189 synthetic method Methods 0.000 title claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 49
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000004821 distillation Methods 0.000 claims abstract description 11
- 230000007935 neutral effect Effects 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 20
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002274 desiccant Substances 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- 239000001110 calcium chloride Substances 0.000 claims description 5
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- ORIYNSKCWVSBFJ-UHFFFAOYSA-N C(CO)(=O)NC(=O)N.[Br] Chemical compound C(CO)(=O)NC(=O)N.[Br] ORIYNSKCWVSBFJ-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000011017 operating method Methods 0.000 abstract description 2
- 230000000977 initiatory effect Effects 0.000 abstract 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 10
- 238000001514 detection method Methods 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses the synthetic method of a kind of Cyclopropylmetyl bromide, belongs to technical field of organic synthesis, comprises the following steps: joined by bromating agent in organic solvent, stirs to all dissolving, obtains bromating agent solution；Bromating agent solution is joined in catalyst and cyclopropyl-carbinol, heat up and carry out back flow reaction；Distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, is dried, obtain Cyclopropylmetyl bromide product.The present invention is with bromating agent and cyclopropyl-carbinol as initiation material, Cyclopropylmetyl bromide product is prepared under the effect of catalyst, have employed the operating procedure of brand-new production technology, reaction yield reaches as high as more than 98%, and low cost, product quality are high, reaction condition is gentle, easily controllable.
Description
Technical field
The present invention relates to technical field of organic synthesis, particularly to the synthetic method of a kind of Cyclopropylmetyl bromide.
Background technology
Bromomethyl cyclopropane is the intermediate that pharmaceutical synthesis is the most important, and root its synthetic method according to the literature is more.
Preparing bromomethyl cyclopropane with cyclopropyl-carbinol for raw material, bromating agent used has phosphorus tribromide and the dibromide of triphen phosphorus.
Use phosphorus tribromide to make bromating agent, have rearrangement product to produce；Use the dibromide of triphen phosphorus as bromating agent, raw material used
Triphenyl phosphorus is expensive, consumption is big.To this end, this patent is with DBDMH, N-bromoacetamide, N-bromo-succinimide etc. as bromine
Agent, using lower fatty acid as reaction catalyst, cyclopropyl-carbinol is made bromomethyl cyclopropane, yield reach 98% with
On, the response time is short, and product purity is high.
Summary of the invention
The present invention provides the synthetic method of a kind of Cyclopropylmetyl bromide, solves the synthetic method of existing Cyclopropylmetyl bromide
Problem relatively costly, that pollution is bigger.
For solving above-mentioned technical problem, the technical scheme is that
The synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) bromating agent is joined in organic solvent, stir to all dissolving, obtain bromating agent solution；
(2) bromating agent solution is joined in catalyst and cyclopropyl-carbinol, heat up and carry out back flow reaction；
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, is dried, obtain Cyclopropylmetyl bromide and produce
Product.
Wherein it is preferred to, described bromating agent is any one in DBDMH, N-bromoacetamide, N-bromo-succinimide
Plant or several.
Wherein it is preferred to, described organic solvent is any in acetone, chloroform, dichloroethanes, DMF, DMSO, DMAC
One or more, the consumption of described organic solvent is 2～5 times of bromating agent quality.
Wherein it is preferred to, described bromating agent is 0.5～2.5:1 with the mol ratio of described cyclopropyl-carbinol.
Wherein it is preferred to, described catalyst is lower fatty acid, and described catalyst charge is cyclopropyl-carbinol quality
0.2%-5%.
Wherein it is preferred to, described lower fatty acid is any one or a few in formic acid, acetic acid, propanoic acid.
The temperature of described back flow reaction is 60 DEG C-160 DEG C, and the response time is 2-10 hour.
Wherein it is preferred to, the temperature of described rectification is 105 DEG C-110 DEG C.
Wherein it is preferred to, the desiccant used in described drying steps is to appoint in calcium chloride, magnesium chloride, anhydrous sodium sulfate
Anticipate one or more.
Beneficial effects of the present invention:
The synthetic method of a kind of Cyclopropylmetyl bromide that the present invention proposes, former for initiateing with cyclopropyl-carbinol with bromating agent
Material, prepares Cyclopropylmetyl bromide product under the effect of catalyst, have employed the operating procedure of brand-new production technology, reaction
Yield reaches as high as more than 98%, and low cost, product quality are high, reaction condition is gentle, easily controllable.
Detailed description of the invention
Below the technical scheme in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment
It is only a part of embodiment of the present invention rather than whole embodiments.Based on the embodiment in the present invention, the common skill in this area
The every other embodiment that art personnel are obtained under not making creative work premise, broadly falls into the model of present invention protection
Enclose.
The synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) bromating agent is joined in organic solvent, stir to all dissolving, obtain bromating agent solution；
(2) bromating agent solution is joined in catalyst and cyclopropyl-carbinol, heat up and carry out back flow reaction；
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, is dried, obtain Cyclopropylmetyl bromide and produce
Product.
Embodiment 1
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) DBDMH is joined in acetone, stir to all dissolving, obtain DBDMH solution；Wherein, organic solvent
Consumption is bromating agent quality 4 times；
(2) bromating agent solution is joined in formic acid and cyclopropyl-carbinol, heat up and carry out back flow reaction, the temperature of back flow reaction
Degree is 100 DEG C, and the response time is 6 hours；Wherein, bromating agent is 1:1 with the mol ratio of cyclopropyl-carbinol；Formic acid addition is ring
The 3% of propyl carbinol quality.
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 108 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is calcium chloride.
The present embodiment synthetic method yield 98.5%, through the content 99.56% of gas chromatographic detection Cyclopropylmetyl bromide.
Embodiment 2
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) N-bromoacetamide is joined in chloroform, stir to all dissolving, obtain N-bromoacetamide solution；Wherein, organic
The consumption of solvent is 24 times of bromating agent quality；
(2) bromating agent solution is joined in acetic acid and cyclopropyl-carbinol, heat up and carry out back flow reaction, the temperature of back flow reaction
Degree is 60 DEG C, and the response time is 10 hours；Wherein, bromating agent is 0.5:1 with the mol ratio of cyclopropyl-carbinol；Acetic acid addition is
The 0.2% of cyclopropyl-carbinol quality.
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 105 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is magnesium chloride.
The present embodiment synthetic method yield 98.6%, through the content 99.62% of gas chromatographic detection Cyclopropylmetyl bromide.
Embodiment 3
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) N-bromo-succinimide is joined in dichloroethanes, stir to all dissolving, obtain N-bromo-succinimide molten
Liquid；Wherein, the consumption of organic solvent is 5 times of bromating agent quality；
(2) bromating agent solution is joined in propanoic acid and cyclopropyl-carbinol, heat up and carry out back flow reaction, the temperature of back flow reaction
Degree is 160 DEG C, and the response time is 2 hours；Wherein, bromating agent is 2.5:1 with the mol ratio of cyclopropyl-carbinol；Propanoic acid addition is
The 5% of cyclopropyl-carbinol quality；
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 110 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is anhydrous sodium sulfate.
The present embodiment synthetic method yield 98.4%, through the content 99.63% of gas chromatographic detection Cyclopropylmetyl bromide.
Embodiment 4
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) DBDMH, N-bromoacetamide are joined in DMF, stir to all dissolving, obtain bromating agent solution；Wherein,
The consumption of organic solvent is 3 times of bromating agent quality；The quality of DBDMH and N-bromoacetamide is 1:1；
(2) bromating agent solution is joined in formic acid and cyclopropyl-carbinol, heat up and carry out back flow reaction, the temperature of back flow reaction
Degree is 80 DEG C, and the response time is 8 hours；Wherein, bromating agent is 1.2:1 with the mol ratio of cyclopropyl-carbinol；Formic acid addition is
The 1% of cyclopropyl-carbinol quality.
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 106 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is calcium chloride.
The present embodiment synthetic method yield 98.7%, through the content 99.52% of gas chromatographic detection Cyclopropylmetyl bromide.
Embodiment 5
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) N-bromoacetamide, N-bromo-succinimide are joined in DMSO, stir to all dissolving, obtain bromating agent molten
Liquid；Wherein, the consumption of organic solvent is 4 times of bromating agent quality；The mass ratio of N-bromoacetamide and N-bromo-succinimide is
2:1；
(2) bromating agent solution is joined in acetic acid and cyclopropyl-carbinol, heat up and carry out back flow reaction, the temperature of back flow reaction
Degree is 120 DEG C, and the response time is 4 hours；Wherein, bromating agent is 1.8:1 with the mol ratio of cyclopropyl-carbinol；Acetic acid addition is
The 2% of cyclopropyl-carbinol quality.
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 107 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is anhydrous sodium sulfate.
The present embodiment synthetic method yield 98.5%, through the content 99.59% of gas chromatographic detection Cyclopropylmetyl bromide.
Embodiment 6
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) DBDMH, N-bromoacetamide, N-bromo-succinimide are joined in DMAC, stir to all dissolving,
Bromating agent solution；Wherein, the consumption of organic solvent is 5 times of bromating agent quality；DBDMH, N-bromoacetamide, N-bromine fourth two
Imido mass ratio is 1:1:1；
(2) bromating agent solution is joined in acetic acid and cyclopropyl-carbinol, heat up and carry out back flow reaction, the temperature of back flow reaction
Degree is 110 DEG C, and the response time is 6 hours；Wherein, bromating agent is 2.0:1 with the mol ratio of cyclopropyl-carbinol；Acetic acid addition is
The 4% of cyclopropyl-carbinol quality.
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 109 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is the calcium chloride of mass ratio 1:1, magnesium chloride.
The present embodiment synthetic method yield 98.4%, through the content 99.49% of gas chromatographic detection Cyclopropylmetyl bromide.
Embodiment 7
This enforcement provides the synthetic method of a kind of Cyclopropylmetyl bromide, comprises the following steps:
(1) DBDMH, N-bromo-succinimide are joined in chloroform, dichloroethanes, stir to all dissolving, obtain bromine
Agent solution；Wherein, the consumption of organic solvent is 3 times of bromating agent quality；DBDMH and the quality of N-bromo-succinimide
Ratio is 1:2；Chloroform, the volume ratio of dichloroethanes are 1:1；
(2) joining in formic acid, acetic acid and cyclopropyl-carbinol by bromating agent solution, heat up and carry out back flow reaction, backflow is anti-
The temperature answered is 90 DEG C, and the response time is 9 hours；Wherein, bromating agent is 2.1:1 with the mol ratio of cyclopropyl-carbinol；Formic acid, second
Acid addition is the 3.5% of cyclopropyl-carbinol quality.Wherein, the volume ratio of formic acid and acetic acid is 1:1；
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, and the temperature of rectification is 108 DEG C, is dried,
To Cyclopropylmetyl bromide product.Wherein, the desiccant used in drying steps is magnesium chloride.
The present embodiment synthetic method yield 98.8%, through the content 99.49% of gas chromatographic detection Cyclopropylmetyl bromide.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all essences in the present invention
Within god and principle, any modification, equivalent substitution and improvement etc. made, should be included within the scope of the present invention.
Claims (9)
1. the synthetic method of a Cyclopropylmetyl bromide, it is characterised in that comprise the following steps:
(1) bromating agent is joined in organic solvent, stir to all dissolving, obtain bromating agent solution；
(2) bromating agent solution is joined in catalyst and cyclopropyl-carbinol, heat up and carry out back flow reaction；
(3) distillation organic solvent, regulation pH, to neutral, wash, is layered, rectification, is dried, obtain Cyclopropylmetyl bromide product.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that described bromating agent is two
Any one or a few in bromine glycolylurea, N-bromoacetamide, N-bromo-succinimide.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that described organic solvent is
Any one or a few in acetone, chloroform, dichloroethanes, DMF, DMSO, DMAC, the consumption of described organic solvent is bromating agent
2～5 times of quality.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that described bromating agent and institute
The mol ratio stating cyclopropyl-carbinol is 0.5～2.5:1.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that described catalyst is low
Level fatty acid, described catalyst charge is the 0.2%-5% of cyclopropyl-carbinol quality.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 5, it is characterised in that described lower fatty acid
For any one or a few in formic acid, acetic acid, propanoic acid.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that described back flow reaction
Temperature is 60 DEG C-160 DEG C, and the response time is 2-10 hour.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that the temperature of described rectification
It it is 105 DEG C-110 DEG C.
The synthetic method of a kind of Cyclopropylmetyl bromide the most according to claim 1, it is characterised in that in described drying steps
Use desiccant be in calcium chloride, magnesium chloride, anhydrous sodium sulfate any one or a few.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110243982A (en) * | 2019-06-25 | 2019-09-17 | 中昊(大连)化工研究设计院有限公司 | Method for detecting cyclopropyl bromine content in sample by gas chromatography |
| US10633375B2 (en) | 2016-08-31 | 2020-04-28 | Jinagsu Hengrui Medicine Co., Ltd | Oxopicolinamide derivative, preparation method therefor and pharmaceutical use thereof |
| CN113402358A (en) * | 2021-07-08 | 2021-09-17 | 中昊(大连)化工研究设计院有限公司 | Novel synthesis method of cyclopropyl bromide |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6118032A (en) * | 1999-08-03 | 2000-09-12 | Eastman Chemical Company | Process for the production of cyclopropylmethyl halides |
| CN101209953A (en) * | 2006-12-30 | 2008-07-02 | 上海药明康德新药开发有限公司 | Applied synthesis method for bromocyclobutane |
| JP2011173838A (en) * | 2010-02-25 | 2011-09-08 | Tosoh Organic Chemical Co Ltd | Process for manufacturing bromomethylcyclopropanes |
| CN103435439A (en) * | 2013-09-09 | 2013-12-11 | 成都红胜科技发展有限公司 | Preparation method of bromomethyl cyclobutane |
| CN104892355A (en) * | 2015-06-12 | 2015-09-09 | 沧州普瑞东方科技有限公司 | Novel method for synthesizing cyclopropyl bromide |
-
2016
- 2016-07-08 CN CN201610537776.6A patent/CN106242941B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6118032A (en) * | 1999-08-03 | 2000-09-12 | Eastman Chemical Company | Process for the production of cyclopropylmethyl halides |
| CN101209953A (en) * | 2006-12-30 | 2008-07-02 | 上海药明康德新药开发有限公司 | Applied synthesis method for bromocyclobutane |
| JP2011173838A (en) * | 2010-02-25 | 2011-09-08 | Tosoh Organic Chemical Co Ltd | Process for manufacturing bromomethylcyclopropanes |
| CN103435439A (en) * | 2013-09-09 | 2013-12-11 | 成都红胜科技发展有限公司 | Preparation method of bromomethyl cyclobutane |
| CN104892355A (en) * | 2015-06-12 | 2015-09-09 | 沧州普瑞东方科技有限公司 | Novel method for synthesizing cyclopropyl bromide |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10633375B2 (en) | 2016-08-31 | 2020-04-28 | Jinagsu Hengrui Medicine Co., Ltd | Oxopicolinamide derivative, preparation method therefor and pharmaceutical use thereof |
| US11084808B2 (en) | 2016-08-31 | 2021-08-10 | Jiangsu Hengrui Medicine Co., Ltd. | Oxopicolinamide derivative, preparation method therefor and pharmaceutical use thereof |
| CN110243982A (en) * | 2019-06-25 | 2019-09-17 | 中昊(大连)化工研究设计院有限公司 | Method for detecting cyclopropyl bromine content in sample by gas chromatography |
| CN113402358A (en) * | 2021-07-08 | 2021-09-17 | 中昊(大连)化工研究设计院有限公司 | Novel synthesis method of cyclopropyl bromide |
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