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Process for preparing 4'-trifluoro methyl-2-diphenyl formic acid

A technology of bibenzoic acid and trifluoromethyl, which is applied in the field of preparation of 4'-trifluoromethyl-2-bibenzoic acid, can solve the problems of tediousness, many by-products, large equipment investment and the like, and achieves simple handling, Inexpensive effect

Inactive Publication Date: 2007-04-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The following deficiencies in the above method: method 1) involves high pressure and gas operation, equipment investment is large, and is also more loaded down with trivial details; Although method 2) is simple to operate, the reaction yield is low, there are many by-products, and purification is difficult; method 3) synthetic route Long and cumbersome; method 4) uses potassium permanganate, which is more polluting

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 1) Under the protection of nitrogen, p-chlorobenzotrifluoride and magnesium chips in a molar ratio of 1:1 were added to anhydrous tetrahydrofuran for reflux reaction to prepare the Grignard reagent.

[0020] 2) o-chlorobenzonitrile, 1,2-bis(diphenylphosphine)ethane nickel chloride and anhydrous tetrahydrofuran were mixed and stirred, then added dropwise to the above-mentioned Grignard reagent for reaction, the reaction temperature was -30°C, and the dropwise addition time was 10 hours; after dripping, filter and precipitate to recover tetrahydrofuran, add toluene and ammonium chloride aqueous solution, and obtain 4'-trifluoromethyl-2-cyanobiphenyl toluene solution after oil-water separation; o-chlorobenzonitrile and p-chloro The molar ratio of trifluorotoluene is 1:0.8, and the molar ratio of 1,2-bis(diphenylphosphine)ethane nickel chloride to p-chlorobenzotrifluoride is 0.01:1.

[0021] 3) The above-mentioned toluene solution is heated and hydrolyzed in an aqueous sodi...

Embodiment 2

[0023] 1) Under the protection of nitrogen, p-chlorobenzotrifluoride and magnesium chips in a molar ratio of 1:1.5 were added to anhydrous tetrahydrofuran for reflux reaction to prepare the Grignard reagent.

[0024] 2) o-chlorobenzonitrile, 1,2-bis(diphenylphosphine)ethane nickel chloride and anhydrous tetrahydrofuran were mixed and stirred, then added dropwise to the above Grignard reagent for reaction, the reaction temperature was 50°C, and the dropwise addition time was 1 hours; after dripping, filter and precipitate to recover tetrahydrofuran, add toluene and ammonium chloride aqueous solution, and obtain the toluene solution of 4'-trifluoromethyl-2-cyanobiphenyl after oil-water separation; o-chlorobenzonitrile and p-chlorotris The molar ratio of fluorotoluene is 1:1.2, and the molar ratio of 1,2-bis(diphenylphosphine)ethane nickel chloride to p-chlorobenzotrifluoride is 0.1:1.

[0025] 3) The above-mentioned toluene solution is heated and hydrolyzed in an aqueous sodium ...

Embodiment 3

[0027] 1) Under the protection of nitrogen, p-chlorobenzotrifluoride and magnesium chips in a molar ratio of 1:1.1 were added to anhydrous tetrahydrofuran for reflux reaction to prepare the Grignard reagent.

[0028] 2) o-chlorobenzonitrile, 1,2-bis(diphenylphosphine)ethane nickel chloride and anhydrous tetrahydrofuran were mixed and stirred, then added dropwise to the above-mentioned Grignard reagent for reaction, the reaction temperature was -10°C, and the dropwise addition time was 5 hours; after dripping, filter and precipitate to recover tetrahydrofuran, add toluene and ammonium chloride aqueous solution, and obtain 4'-trifluoromethyl-2-cyanobiphenyl toluene solution after oil-water separation; o-chlorobenzonitrile and p-chloro The molar ratio of trifluorotoluene is 1:1.1, and the molar ratio of 1,2-bis(diphenylphosphine)ethane nickel chloride to p-chlorobenzotrifluoride is 0.02:1.

[0029] 3) The above-mentioned toluene solution is heated and hydrolyzed in an aqueous sod...

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Abstract

The present invention discloses process of preparing 4'-trifluoro methyl-2-diphenic acid. The process includes the following steps: 1. the reflux reaction of p-chloro trifluorotoluene and magnesium chip in anhydrous tetrahydrofuran under nitrogen protection to obtain Grignard reagent; 2. mixing o-chloro phenyl nitrile, 1, 2-bis(diphenyl phosphine) ethane nickel chloride and tetrahydrofuran via stirring; dropping the Grignard reagent; filtering and eliminating solvent to recover tetrahydrofuran; adding toluene and water solution of ammonium chloride; and oil-water separating to obtain toluene solution of 4'- trifluoro methyl-2-cyan diphenyl; and 3. heating the toluene solution in alkaline water solution to hydrolyze; oil-water separation to obtain water solution of 4'-trifluoro methyl-2-diphenic sodium and further treatment to obtain 4'-trifluoro methyl-2-diphenic acid. The process has high yield, low cost and other advantages, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to the preparation method of biphenylcarboxylic acid compound, relate in particular to a kind of preparation method of 4'-trifluoromethyl-2-biphenylcarboxylic acid. Background technique [0002] The method of the synthetic 4 '-trifluoromethyl-2-biphenylformic acid of present report mainly contains following method: [0003] 1) Synthesize 4'-trichloromethyl-2-cyanobiphenyl from 4'-methyl-2-cyanobiphenyl by introducing chlorine gas, and then use hydrogen fluoride gas to fluorinate under high pressure into 4'-trifluoromethyl-2 -Cyanobiphenyl, finally hydrolyzed to generate 4'-trifluoromethyl-2-biphenylcarboxylic acid; see Japanese Patent JP2004067521 and European Patent EP1223158 for details. [0004] 2) Condensation of p-trifluoromethyl chlorobenzene and methyl o-chlorobenzoate in the presence of pyridine, nickel chloride and zinc powder into 4'-trifluoromethyl-2-biphenylcarboxylate, and then hydrolyzed into 4'-trifluorome...

Claims

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Application Information

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IPC IPC(8): C07C63/331C07C51/08
Inventor 李伟军林旭锋陈卫祥
Owner ZHEJIANG UNIV
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