CN104478725A - Method for preparing 4'-chloro-2-nitro biphenyl - Google Patents
Method for preparing 4'-chloro-2-nitro biphenyl Download PDFInfo
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- CN104478725A CN104478725A CN201410692141.4A CN201410692141A CN104478725A CN 104478725 A CN104478725 A CN 104478725A CN 201410692141 A CN201410692141 A CN 201410692141A CN 104478725 A CN104478725 A CN 104478725A
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- chloro
- acid
- ortho
- nitro biphenyl
- palladium diacetate
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- 238000000034 method Methods 0.000 title claims abstract description 16
- OMNWKPZIFZJANV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-nitrobenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=C(Cl)C=C1 OMNWKPZIFZJANV-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000002904 solvent Substances 0.000 claims abstract description 29
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims abstract description 28
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract description 28
- 239000002994 raw material Substances 0.000 claims abstract description 16
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- ZOQCZTRFTARYGJ-UHFFFAOYSA-N chlorooxy(phenyl)borinic acid Chemical compound ClOB(O)C1=CC=CC=C1 ZOQCZTRFTARYGJ-UHFFFAOYSA-N 0.000 claims description 28
- QIFZRTGHATXWQI-UHFFFAOYSA-N 1-chloro-2-nitro-3-phenylbenzene Chemical group [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CC=CC=C1 QIFZRTGHATXWQI-UHFFFAOYSA-N 0.000 claims description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 150000002940 palladium Chemical class 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical compound NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 abstract 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 abstract 2
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 230000006837 decompression Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000011084 recovery Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 238000010792 warming Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000005740 Boscalid Substances 0.000 description 3
- 229940118790 boscalid Drugs 0.000 description 3
- -1 boscalid amine Chemical class 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 2
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 1
- YOJKKXRJMXIKSR-UHFFFAOYSA-N 1-nitro-2-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1 YOJKKXRJMXIKSR-UHFFFAOYSA-N 0.000 description 1
- RXTRRIFWCJEMEL-UHFFFAOYSA-N 2-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1Cl RXTRRIFWCJEMEL-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000005784 autoimmunity Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for preparing 4'-chloro-2-nitro biphenyl. The method comprises the following step: by taking p-chlorophenylboronic acid and o-nitrophenylhydrazine as raw materials, palladium diacetate as a catalyst, 2, 2-dimethylpropionic acid as a cocatalyst and triphenyl phosphine as a ligand, carrying out reaction in a solvent under a heating condition to obtain 4'-chloro-2-nitro biphenyl, wherein the molar ratio of p-chlorophenylboronic acid, o-nitrophenylhydrazine, palladium diacetate, triphenyl phosphine and 2, 2-dimethylpropionic acid is 1: (1-1.05): (0.025-0.075): (0.2-0.5): (1-1.8). According to the method provided by the invention, the proportion and reaction temperature of the raw materials are screened, so that a relatively optimal preparation method is obtained. The method has the advantages of low cost, simple operation, less environmental pollution, relatively high yield and the like.
Description
Technical field
The present invention relates to a kind of method preparing the chloro-2 nitro biphenyl of 4'-.The chloro-2 nitro biphenyl of 4'-can be used as the important intermediate of agricultural bactericide boscalid amine.
Background technology
The chloro-2 nitro biphenyl of 4'-is the important intermediate of Novel tobacco acid amide fungicides boscalid amine.The chloro-2 nitro biphenyl of 4'-after iron powder or the reduction of other reductive agents, then reacts with 2-chloronicotinoyl chloride and just obtains boscalid amine.
The current synthetic method that the chloro-2 nitro biphenyl of 4'-is reported at present and problem are:
1) be obtained by reacting chlorophenylboronic acid and adjacent halogen oil of mirbane, can only select bromo-derivative in reaction, though the cheap yield of chloro thing is low, reaction easily generates autoimmunity syndrome product, separation difficulty;
2) o-Carboxynitrobenzene and para chlorobromobenzene are under palladium catalyst catalysis, and in polar solvent, pyroreaction obtains; This temperature of reaction height by product is more, and separation yield is generally lower;
3) 4-chlordiphenyl obtains through nitration mixture acidifying, and nitration mixture has severe corrosive, suitability for industrialized production difficulty;
4) 2 nitro biphenyl and chlorine obtain through tin tetraiodide catalysis chloro, and chlorine is wayward in the reaction, and easily generate many chloro-products, and exquisite cost is high.
Summary of the invention
The invention provides a kind of novel method of synthesizing the chloro-2 nitro biphenyl of 4'-, with to chlorophenylboronic acid and ortho-nitrophenyl hydrazine for raw material, under solutions of weak acidity, palladium diacetate catalysis triphenyl phosphorus does part and obtains through linked reaction.Reaction formula structural formula is as follows:
The present invention relates to the preparation method of the chloro-2 nitro biphenyl of 4'-, the method is characterized in that:
Adopting chlorophenylboronic acid and ortho-nitrophenyl hydrazine is raw material, and select palladium class catalyzer, weak acid as promotor, triphenyl phosphorus is part, reacts in a solvent under heating condition, generates the chloro-2 nitro biphenyl of 4'-;
In described step, palladium class catalyzer is palladium diacetate;
In described step, weak acid adopts organic monoacid PA or its isomers, preferred PA.
Solvent in described step is N-Methyl pyrrolidone or N,N-dimethylacetamide.
Heating condition in described step is temperature of reaction is 60 ~ 120 DEG C.Peak optimization reaction temperature is 85 ~ 95 DEG C.
Detailed description optimum condition is as follows:
In described step, to chlorophenylboronic acid and ortho-nitrophenyl hydrazine in a solvent, under catalyst action, triphenylphosphine reacts as under part slightly acidic heating condition, until raw material reaction completely after, reaction solution is lowered the temperature; Decompression and solvent recovery, then adds sherwood oil in reaction solution, filters, and by dried over mgso after filtrate washing, steams solvent and obtains the chloro-2 nitro biphenyl of product 4'-.
The method preferred proportion: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: the mol ratio of PA is 1:(1 ~ 1.05): (0.025 ~ 0.075): (0.2 ~ 0.5): (1 ~ 1.8);
Preferred proportion is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: PA=1:1.02:0.05:0.3:1.5.
To the present invention is directed in linked reaction the influence factor of yield as catalyst levels, reaction solvent, temperature of reaction, reaction times and solvent recuperation number etc. have carried out screening study, find a method that operation is comparatively easy, yield is higher.
Embodiment
Below, by the specific embodiment under different mol ratio, the present invention will be described in more detail.Yield represents with molecular fraction.
Embodiment 1
15.6g to chlorophenylboronic acid, 15.6g ortho-nitrophenyl hydrazine joins in 50 milliliters of N-Methyl pyrrolidone, then 15g 2 is added successively, 2-neopentanoic acid, 1.2g palladium diacetate, 9.1g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.02:0.05:0.3:1.5), be warming up to 90 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 70 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 18.9g of product 4'-, yield 81%.
Embodiment 2
15.6g to chlorophenylboronic acid, 15.3g ortho-nitrophenyl hydrazine joins in 50 milliliters of N-Methyl pyrrolidone, then 10.2g 2 is added successively, 2-neopentanoic acid, 0.6g palladium diacetate, 6.1g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1:0.025:0.2:1), be warming up to 60 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 70 milliliters of sherwood oils are added, filter, by dried over mgso after filtrate washing, steam solvent and obtain the chloro-2 nitro biphenyl 15.1g of product 4'-, yield 65%.
Embodiment 3
15.6g to chlorophenylboronic acid, 16.1g ortho-nitrophenyl hydrazine joins in 50 milliliters of N-Methyl pyrrolidone, then 18.3g 2 is added successively, 2-neopentanoic acid, 1.7g palladium diacetate, 15.2g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.05:0.075:0.5:1.8), be warming up to 90 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 70 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 19.1g of product 4'-, yield 82%.
Embodiment 4
15.6g to chlorophenylboronic acid, 15.7g ortho-nitrophenyl hydrazine joins in 50 milliliters of N-Methyl pyrrolidone, then 14.3g 2 is added successively, 2-neopentanoic acid, 1.34g palladium diacetate, 10.6g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.03:0.06:0.35:1.4), be warming up to 120 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 70 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 17g of product 4'-, yield 73%.
Embodiment 5
15.6g to chlorophenylboronic acid, 16.1g ortho-nitrophenyl hydrazine joins 50 milliliters of N, in N-N,N-DIMETHYLACETAMIDE, then 18.3g 2 is added successively, 2-neopentanoic acid, 1.7g palladium diacetate, 15.2g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.05:0.075:0.5:1.8), be warming up to 90 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 50 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 17.4g of product 4'-, yield 75%.
Embodiment 6
15.6g to chlorophenylboronic acid, 15.6g ortho-nitrophenyl hydrazine joins 50 milliliters of N, in N-N,N-DIMETHYLACETAMIDE, then 15g 2 is added successively, 2-neopentanoic acid, 1.2g palladium diacetate, 9.1g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.02:0.05:0.3:1.5), be warming up to 60 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 45 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 16.5g of product 4'-, yield 71%.
Embodiment 7
15.6g to chlorophenylboronic acid, 15.3g ortho-nitrophenyl hydrazine joins 50 milliliters of N, in N-N,N-DIMETHYLACETAMIDE, then 10.2g 2 is added successively, 2-neopentanoic acid, 0.6g palladium diacetate, 6.1g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1:0.025:0.2:1), be warming up to 120 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 40 milliliters of sherwood oils are added, filter, by dried over mgso after filtrate washing, steam solvent and obtain the chloro-2 nitro biphenyl 15.5g of product 4'-, yield 67%.
Embodiment 8
15.6g to chlorophenylboronic acid, 15.3g ortho-nitrophenyl hydrazine joins 50 milliliters of N, in N-N,N-DIMETHYLACETAMIDE, then 11.2g 2 is added successively, 2-neopentanoic acid, 0.66g palladium diacetate, 8.18g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.02:0.03:0.27:1.1), be warming up to 90 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 50 milliliters of sherwood oils are added, filter, by dried over mgso after filtrate washing, steam solvent and obtain the chloro-2 nitro biphenyl 16.4g of product 4'-, yield 70.6%.
Embodiment 9
15.6g to chlorophenylboronic acid, 16.1g ortho-nitrophenyl hydrazine joins 50 milliliters and reclaims in N-Methyl pyrrolidone, then 18.3g 2 is added successively, 2-neopentanoic acid, 1.7g palladium diacetate, 15.2g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.05:0.075:0.5:1.8), be warming up to 85 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 70 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 18.4g of product 4'-, yield 79.5%.
Embodiment 10
15.6g to chlorophenylboronic acid, 15.6g ortho-nitrophenyl hydrazine joins 50 milliliters and reclaims N, in N-N,N-DIMETHYLACETAMIDE, then 15g 2 is added successively, 2-neopentanoic acid, 1.2g palladium diacetate, 9.1g triphenylphosphine (mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: trimethylacetic acid=1:1.02:0.05:0.3:1.5), be warming up to 95 DEG C of reactions, after raw material reaction is complete, reaction solution is lowered the temperature, decompression and solvent recovery, then in reaction solution, 30 milliliters of sherwood oils are added, filter, filtrate uses dried over mgso with after dilute hydrochloric acid washing, steam solvent and obtain the chloro-2 nitro biphenyl 16.9g of product 4'-, yield 73%.
Claims (5)
1. prepare a method for the chloro-2 nitro biphenyl of 4'-, it is characterized in that:
Adopting chlorophenylboronic acid and ortho-nitrophenyl hydrazine is raw material, and select palladium class catalyzer, weak acid as promotor, triphenyl phosphorus is part, reacts in a solvent under heating condition, obtains the chloro-2 nitro biphenyl of 4'-.
2. the method for claim 1, is characterized in that described palladium class catalyzer is palladium diacetate.
3. the method for claim 1, is characterized in that described weak acid is: PA.
4. the method for claim 1, it is characterized in that described solvent is: N-Methyl pyrrolidone, also can be N,N-dimethylacetamide.
5. the method for claim 1, its characteristic reaction mol ratio is: to chlorophenylboronic acid: ortho-nitrophenyl hydrazine: palladium diacetate: triphenyl phosphorus: the mol ratio of PA is 1:(1 ~ 1.05): (0.025 ~ 0.075): (0.2 ~ 0.5): (1 ~ 1.8).
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| CN201410692141.4A CN104478725A (en) | 2014-11-25 | 2014-11-25 | Method for preparing 4'-chloro-2-nitro biphenyl |
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| CN201410692141.4A CN104478725A (en) | 2014-11-25 | 2014-11-25 | Method for preparing 4'-chloro-2-nitro biphenyl |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997033846A1 (en) * | 1996-03-13 | 1997-09-18 | Basf Aktiengesellschaft | Process for preparing nitrobiphenylene |
| WO2006092429A1 (en) * | 2005-03-02 | 2006-09-08 | Basf Aktiengesellscahft | Method for producing substituted biphenyls |
| JP2011001349A (en) * | 2009-05-20 | 2011-01-06 | Tosoh Corp | 2-aminocarbazole compound and application thereof |
| WO2012086576A1 (en) * | 2010-12-20 | 2012-06-28 | 東ソー株式会社 | Amine compound and organic el element |
| CN103539679A (en) * | 2013-10-17 | 2014-01-29 | 天津市筠凯化工科技有限公司 | Method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis |
-
2014
- 2014-11-25 CN CN201410692141.4A patent/CN104478725A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997033846A1 (en) * | 1996-03-13 | 1997-09-18 | Basf Aktiengesellschaft | Process for preparing nitrobiphenylene |
| WO2006092429A1 (en) * | 2005-03-02 | 2006-09-08 | Basf Aktiengesellscahft | Method for producing substituted biphenyls |
| JP2011001349A (en) * | 2009-05-20 | 2011-01-06 | Tosoh Corp | 2-aminocarbazole compound and application thereof |
| WO2012086576A1 (en) * | 2010-12-20 | 2012-06-28 | 東ソー株式会社 | Amine compound and organic el element |
| CN103539679A (en) * | 2013-10-17 | 2014-01-29 | 天津市筠凯化工科技有限公司 | Method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis |
Non-Patent Citations (4)
| Title |
|---|
| DEY,RAJU 等: "Molecular sieves-supported palladium(II) catalyst: Suzuki coupling of chloroarenes and an easy access to useful intermediates for the synthesis of irbesartan, losartan and boscalid", 《TETRAHEDRON》, vol. 66, no. 13, 4 February 2010 (2010-02-04), pages 2303 - 3 * |
| FELPIN,FRANCOIS-XAVIER 等: "Improved Suzuki-Miyaura reactions of aryldiazonium salts with boronic acids by tuning palladium on charcoal catalyst properties", 《ADVANCED SYNTHESIS & CATALYSIS》, vol. 351, no. 4, 13 February 2009 (2009-02-13), pages 649 - 655 * |
| LIU,FENG-SHOU 等: "Efficient salicylaldimine ligands for a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction", 《APPLIED ORGANOMETALLIC CHEMISTRY》, vol. 26, no. 8, 2 July 2012 (2012-07-02), pages 428 - 3 * |
| PENG,ZHIMIN 等: "Palladium-Catalyzed Suzuki Cross-Coupling of Arylhydrazines via C-N Bond Cleavage", 《JOURNAL OF ORGANIC CHEMISTRY》, vol. 79, no. 6, 21 February 2014 (2014-02-21), pages 2734 - 1 * |
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Application publication date: 20150401 |