CN1409697A - 制备三氟甲基乙酰苯的方法 - Google Patents
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- 238000000034 method Methods 0.000 title claims abstract description 24
- LBWMQVOHFPLVBY-UHFFFAOYSA-N 3,3,3-trifluoro-1-phenylpropan-1-one Chemical class FC(F)(F)CC(=O)C1=CC=CC=C1 LBWMQVOHFPLVBY-UHFFFAOYSA-N 0.000 title abstract 3
- -1 trifluoromethylbenzoyl halide Chemical class 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- FYDUUODXZQITBF-UHFFFAOYSA-N 1-[2-(trifluoromethyl)phenyl]ethanone Chemical class CC(=O)C1=CC=CC=C1C(F)(F)F FYDUUODXZQITBF-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- ABXGMGUHGLQMAW-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C(F)(F)F)=C1 ABXGMGUHGLQMAW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 235000012255 calcium oxide Nutrition 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 235000012204 lemonade/lime carbonate Nutrition 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 235000014692 zinc oxide Nutrition 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
- 230000020477 pH reduction Effects 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- YWQNAFUPXWKYRS-UHFFFAOYSA-N morpholin-4-yl-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2CCOCC2)=C1 YWQNAFUPXWKYRS-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明提供了一种用于制备通式(I)的三氟甲基乙酰苯的新方法，通式(I)中芳香环上的CF3基团的位置可以是在相对于乙酰基的2或3位，该方法包括：(a)使通式(II)的三氟甲基苯甲酰氯与通式(III)的环形仲胺在用来作为酸受体的碱水溶液存在下反应，通式(II)中芳香环上CF3基团的位置可以是相对于乙酰基的2或3位，Hal是选自氟、氯、溴和碘的卤原子，通式(III)中A是一个可以间插着氧或硫原子的C3－C7亚烷基桥键，反应结果形成通式(IV)的环烷基三氟甲基苯甲酰胺，其中CF3基团在芳香环上的位置和A的定义同上，以及(b)向该环烷基三氟甲基苯甲酰胺中加入甲基卤化镁，随后用酸化剂水溶液酸化，形成式(I)的三氟甲基乙酰苯。
Description
本发明涉及制备三氟甲基乙酰苯类、特别是制备3-三氟甲基乙酰苯的方法。
过去已使用几种方法制备3-三氟甲基乙酰苯，但是它们都不适合大规模的工业制造，大规模的工业制造方法应当是简单和有效的方法，能够由市场上容易得到的试剂出发，以高产率和高纯度提供三氟甲基乙酰苯。
本发明提供了一种使用容易得到的原料以高产率和高纯度制备三氟甲基乙酰苯的方法。另外，该方法还具有环境保护方面的优点。
本发明方法包括两个步骤：(a)使三氟甲基苯甲酰卤与环形仲胺在碱水溶液存在下反应，形成环烷基三甲基苯甲酰胺，和(b)向该苯甲酰胺中加入甲基卤化镁，随后用乙酸水溶液酸化，形成产物。使用环胺的好处是由于胺的循环使用而减少了废物。
本发明提供了制备通式I的三氟甲基乙酰苯的方法
其中芳香环上的CF3基团的位置可以是相对于乙酰基的2位或3位，该方法包括
(a)通式II的三氟甲基苯甲酰卤与通式III的环胺在作为酸受体的碱水溶液存在下反应
其中芳香环上CF3基团的位置可以是相对于乙酰基的2位或3位，Hal是选自氟、氯、溴和碘的卤原子，其中A是C3-C7亚烷基桥键，它可以间插着氧或硫原子，反应的结果形成通式IV的环烷基-三氟甲基苯甲酰胺其中芳香环上CF3基团的位置及A同以上定义，和
(b)向该环烷基-三氟甲基苯甲酰胺加入甲基卤化镁，随后用酸化剂水溶液酸化，形成式I的三氟甲基乙酰苯。
在本发明的一项优选实施方案中，使用此方法制备3-三氟甲基乙酰苯。
式III的环形仲胺特别有助于这样制备的三氟甲基乙酰苯的高产率和高纯度。
环形仲胺通常代表吡咯烷、哌啶(未被取代的或者有2、3或4位被低级烷基如甲基或乙基取代)，或者最好是吗啉或硫代吗啉。
步骤(a)和(b)的反应通常都在从室温左右(+20℃至25℃)至约+60℃的中等温度下进行。反应物三氟甲基苯甲酰卤是已知的。在实施本发明中特别适用的是3-三氟甲基苯甲酰氯。可作为酸受体使用的碱的实例是氢氧化钠、氢氧化钾、碳酸钾、碳酸氢钾、碳酸钠、碳酸氢钠、碳酸钙、氢氧化钙、氧化锌、氧化钙及其混合物的约5-70％浓度的水溶液。环胺可以是以上定义的式III范围之内的任何环胺和它们中的一种或多种的混合物，但不限于所给出的实例。特别适用于本发明方法的是哌啶和吗啉。本发明方法优选在惰性溶剂中进行，例如醚，如乙醚、甲乙醚、叔丁基甲基醚、四氢呋喃、二氧杂环己烷等。
用于本发明的格氏试剂是采用甲基作为烷基取代基的格氏试剂。典型的代表是I-Mg-CH3、Br-Mg-CH3和Cl-Mg-CH3。
酸化优选用乙酸进行。但在本发明方法中也可以使用其它的酸化剂，例如盐酸、硫酸和氯化胺。
本发明的高纯产物促进了它作为中间体用于制造重要的农用杀真菌剂α-甲氧亚胺基-2-[[[[1-[3-(三氟甲基)苯基]乙烯基]氨基]氧]甲基]苯乙酸甲酯(trifloxystrobin)。
以下实施例说明了本发明。它们并不被认为是以任何方式限制权利要求的范围。实施例1
向装有搅拌器、两上加液漏斗、冷凝管和加热套的750ml烧瓶中加入88g水和45g吗啉。在搅拌下向此混合物中同时加入104.3g(0.5mol)3-三氟甲基苯甲酰氯和40.8g50％NaOH水溶液。加料期间pH保持在9-10之间，温度保持在+40℃和+55℃之间。加完后，将混合物在搅拌下加热30分钟，至55～60℃。加入75g甲苯后，弃去下面的水层。在搅拌下向烧杯中再加入甲苯和水。放置几分钟后，再次去掉下部的水层。减压蒸除上部有机层的溶剂。完全去掉有机层中的甲苯后，分离出4-(3-三氟甲基苯甲酰)吗啉并用于实施例2中。实施例2
向装有搅拌器、冷凝管、干燥氮气氛装置和液面下加料管的1升烧瓶中加入310g四氢呋喃、18g镁屑和少量碘晶体。将混合物在温和的搅拌下加热至+50℃。通过液面下加料管向此混合物中加入41.1g氯甲烷，保持温度在+50℃和+60℃之间。将得到的甲基卤化镁冷却到+30℃。在搅拌下向此格氏试剂溶液中于1-2小时内加入溶在四氢呋喃中的4-(3-三氟甲基苯甲酰)吗啉(如实施例1中制得的)。加完后将混合物加热至+35～+40℃并搅拌18小时。
向另一只有类似装备的1升烧瓶中加入90g乙酸和205g水。在搅拌下将上述的格氏试剂混合物加到这个第二只烧瓶中。然后使所形成的混合物分层。去掉下部的水层，用饱和盐水将上部的有机层洗几次，然后将有机层在减压下加热以除掉四氢呋喃。除去溶剂后，将产物混合物减压蒸馏，得到纯度98％的3-三氟甲基乙酰苯。
Claims (6)
1.一种制备通式I的三氟甲基乙酰苯类的方法其中芳香环上CF3基团的位置可以是相对于乙酰基的2位或3位，所述方法包括
(a)使通式II的三氟甲基苯甲酰卤与通式III的环形仲胺在作为酸受体的碱水溶液存在下反应
其中芳香环上CF3基团的位置可以是相对于乙酰基的2位或3位，Hal是选自氟、氯、溴和碘的卤原子，其中A是C3-C7亚烷基桥键，可以间插着氧或硫原子，反应结果形成通式IV的环烷基三氟甲基苯甲酰胺其中芳香环上的CF3基团的位置以及A同以上的定义，和
(b)向该环烷基三氟甲基苯甲酰胺中加入甲基卤化镁，随后用酸化剂水溶液酸化，以形成式I的三氟甲基乙酰苯。
2.权利要求1的方法，其中三氟甲基苯甲酰卤是3-三氟甲基苯甲酰氯。
3.权利要求1的方法，其中的环胺是吗啉或硫代吗啉。
4.权利要求1的方法，其中制备了3-三氟甲基乙酰苯。
5.权利要求1的方法，其中碱是选自氢氧化钠、氢氧化钾、碳酸钾、碳酸氢钾、碳酸钠、碳酸氢钠、碳酸钙、氢氧化钙、氧化锌或氧化钙或其混合物。
6.权利要求1的方法，其中的酸化剂是乙酸、盐酸、硫酸或氯化铵或其混合物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9929562.8A GB9929562D0 (en) | 1999-12-14 | 1999-12-14 | Organic compounds |
| GB9929562.8 | 1999-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1409697A true CN1409697A (zh) | 2003-04-09 |
Family
ID=10866309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00816915A Pending CN1409697A (zh) | 1999-12-14 | 2000-10-27 | 制备三氟甲基乙酰苯的方法 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1240127A1 (zh) |
| JP (1) | JP2003517029A (zh) |
| KR (1) | KR20020056943A (zh) |
| CN (1) | CN1409697A (zh) |
| AU (1) | AU1388901A (zh) |
| BR (1) | BR0016320A (zh) |
| GB (1) | GB9929562D0 (zh) |
| HK (1) | HK1052926A1 (zh) |
| IL (1) | IL149713A0 (zh) |
| MX (1) | MXPA02005873A (zh) |
| WO (1) | WO2001044152A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104478792A (zh) * | 2014-12-26 | 2015-04-01 | 西华大学 | 一种具有抑菌活性的化合物及其水溶性液剂的制备方法和应用 |
| CN105566089A (zh) * | 2008-04-09 | 2016-05-11 | 杜邦公司 | 用于制备3-三氟甲基查耳酮的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5211876B2 (ja) * | 2008-06-11 | 2013-06-12 | セントラル硝子株式会社 | 高純度２’−トリフルオロメチルプロピオフェノンの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9808447D0 (en) * | 1998-04-18 | 1998-06-17 | Zeneca Ltd | Process |
| US5969188A (en) * | 1999-01-05 | 1999-10-19 | Nipa Hardwicke, Inc. | Process for producing trifluoromethylacetophenones |
-
1999
- 1999-12-14 GB GBGB9929562.8A patent/GB9929562D0/en not_active Ceased
-
2000
- 2000-10-27 JP JP2001545242A patent/JP2003517029A/ja active Pending
- 2000-10-27 WO PCT/EP2000/010596 patent/WO2001044152A1/en not_active Application Discontinuation
- 2000-10-27 KR KR1020027006569A patent/KR20020056943A/ko not_active Application Discontinuation
- 2000-10-27 AU AU13889/01A patent/AU1388901A/en not_active Abandoned
- 2000-10-27 BR BR0016320-1A patent/BR0016320A/pt not_active Application Discontinuation
- 2000-10-27 IL IL14971300A patent/IL149713A0/xx unknown
- 2000-10-27 CN CN00816915A patent/CN1409697A/zh active Pending
- 2000-10-27 MX MXPA02005873A patent/MXPA02005873A/es unknown
- 2000-10-27 EP EP00975941A patent/EP1240127A1/en not_active Withdrawn
-
2003
- 2003-07-21 HK HK03105240.4A patent/HK1052926A1/zh unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566089A (zh) * | 2008-04-09 | 2016-05-11 | 杜邦公司 | 用于制备3-三氟甲基查耳酮的方法 |
| CN105566089B (zh) * | 2008-04-09 | 2019-07-02 | 杜邦公司 | 用于制备3-三氟甲基查耳酮的方法 |
| CN104478792A (zh) * | 2014-12-26 | 2015-04-01 | 西华大学 | 一种具有抑菌活性的化合物及其水溶性液剂的制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003517029A (ja) | 2003-05-20 |
| BR0016320A (pt) | 2002-08-27 |
| KR20020056943A (ko) | 2002-07-10 |
| AU1388901A (en) | 2001-06-25 |
| MXPA02005873A (es) | 2003-01-28 |
| HK1052926A1 (zh) | 2003-10-03 |
| GB9929562D0 (en) | 2000-02-09 |
| IL149713A0 (en) | 2002-11-10 |
| WO2001044152A1 (en) | 2001-06-21 |
| EP1240127A1 (en) | 2002-09-18 |
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