Method for preparation of 2-benzyl-5-(trifluoromethyl)benzoic acid

A technology of trifluoromethyl benzoic acid and trifluoromethyl, which is applied in the field of preparation of 2-benzyl-5-trifluoromethyl benzoic acid, can solve the problem of high reaction cost, harsh reaction conditions, unsuitable for industrial production, etc. problem, to achieve the effect of high yield and low price

Active Publication Date: 2018-11-06
安徽古尔特科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, using toluene as a benzylation reagent often requires complex and harsh reaction conditions, such as high temperature, expensive transition metal catalysts such as Ru/Rh, etc.
Although the prior art has also reported the use of cheap transition metal catalysts such as Cu or Ni

Method used

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  • Method for preparation of 2-benzyl-5-(trifluoromethyl)benzoic acid
  • Method for preparation of 2-benzyl-5-(trifluoromethyl)benzoic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0024] (1) Add 3-trifluoromethyl-N-(8-quinoline)benzamide (63.2mg, 0.2mmol), DTBP (58.5mg, 0.4mmol), and Co(acac )2 (14.2mg, 0.04mmol), then add 2mL of anhydrous toluene under nitrogen, heat the reaction to 130°C, and stir the reaction for 6 hours. After the reaction was completed, filter and wash with ethyl acetate, the filtrate was spin-dried, and the residual compound was separated by column chromatography on a silica gel column (petroleum ether / ethyl acetate=10 / 1~20 / 1) to obtain intermediate (I). Efficiency 87%, 1H NMR (500MHz, Chloroform-d) δ10.12(s, 1H), 8.86(d, J=6.4Hz, 1H), 8.65–8.60(m, 1H), 8.11(d, J=8.0 Hz,1H),7.85(s,1H),7.55–7.46(m,3H),7.36–7.35(m,1H),7.28(d,J=8.0Hz,1H),7.11–7.01(m,5H) ,4.25(s,2H).

[0025] (2) Add intermediate (I) to a round bottom flask, add 10mL of anhydrous tetrahydrofuran as a solvent, place the round bottom flask under ice bath conditions, then add 15 mg of sodium hydride in batches, stir for a period of time and slowly drop Add 85mg of met...

Embodiment 2

[0028] (1) Add 3-trifluoromethyl-N-(8-quinoline) benzamide (63.2mg, 0.2mmol), DTBP (87.6mg, 0.6mmol), and Co(acac )2 (14.2mg, 0.04mmol), then added 2mL of anhydrous toluene under nitrogen, heated the reaction to 120°C, and stirred for 8 hours. After the reaction was completed, filter and wash with ethyl acetate, the filtrate was spin-dried, and the residual compound was separated by column chromatography on a silica gel column (petroleum ether / ethyl acetate=10 / 1~20 / 1) to obtain intermediate (I). The rate is 89%.

[0029] (2) Add intermediate (I) to a round bottom flask, add 10mL of anhydrous tetrahydrofuran as a solvent, place the round bottom flask under ice bath conditions, then add 15 mg of sodium hydride in batches, stir for a period of time and slowly drop Add 57 mg iodomethane. After reacting at room temperature for 12 hours, pass through a short column of silica gel, rinse the reactor and the sludge above the short column of gelatin with ethyl acetate, wash the filtra...

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PUM

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Abstract

The invention belongs the technical field of organic synthesis, and particularly relates to a method for preparation of 2-benzyl-5-(trifluoromethyl)benzoic acid. The method comprises the steps: enabling N-(8-quinolyl)-3-(trifluoromethyl) benzamide as an original material to be subjected to three steps of reaction including benzylation, methylation, and hydrolysis and acidification, thereby obtaining 2-benzyl-5-(trifluoromethyl) benzoic acid. The benzylation reaction adopts cobalt diacetylacetonate to serve as a catalyst, use of alkali is not needed, and the catalysis system has the advantagesof cheap price and high yield of a target product. A small amount of water is added in the hydrolysis step, to promote hydrolysis of an intermediate, and shorten reaction time and obtain a higher yield of the target product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a preparation method of 2-benzyl-5-trifluoromethylbenzoic acid. Background technique [0002] Diaryl alkane derivatives are a very important class of compounds. Many of these compounds have biological activity or are the skeleton structure of some drugs, such as the anti-cold drug Benadryl, anti-diabetic drugs and some anti-depressant drugs diphenhydramine Lun et al. Because of this, the synthesis of diaryl alkane derivatives has also received extensive attention from organic chemists. At present, one of the traditional and main methods of this kind of compounds is to use the coupling reaction of halides (such as benzyl bromide) and some nucleophiles under the catalysis of transition metals. [0003] Benzene homologues headed by toluene and xylene are bulk industrial products with low price, large output and large reserves. In terms of chemical properties, the la...

Claims

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Application Information

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IPC IPC(8): C07C51/06C07C63/72
CPCC07C51/06C07D215/40C07C63/72
Inventor 黄胜
Owner 安徽古尔特科技有限公司
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