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Synthesis method of 2-trifluoromethyl benzamide

A technology for trifluoromethylbenzamide and trifluoromethylbenzene cyanide, which is applied in the field of organic chemical synthesis, can solve the problems of low 2-trifluoromethylbenzamide yield, large pollution and the like, and achieves easy recovery, The effect of less three wastes and good industrialization prospects

Pending Publication Date: 2021-11-26
内蒙古蓝科生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Therefore, the technical problem to be solved in the present invention is to overcome the defects of low yield and high pollution of 2-trifluoromethylbenzamide in the prior art, thereby providing a kind of mild condition, simple operation, less three wastes and high yield The method for the synthesis of 2-trifluoromethylbenzamide

Method used

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  • Synthesis method of 2-trifluoromethyl benzamide

Examples

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Effect test

Embodiment 1

[0036] 1) Preparation of 2-fluoro-3-chlorobenzotrifluoride

[0037] Add 215g of 2,3-dichlorobenzotrifluoride, 73g of potassium fluoride, 7g of triphenylphosphine bromide and 430mL of 1,3-dimethylimidazolidinone into a 1000mL three-necked flask equipped with a rectification column, and stir to raise the temperature Reflux reaction. After 1 hour of reaction, 185 g of a colorless transparent liquid began to evaporate slowly, and the content of GC analysis was 93.9%, which was 2-fluoro-3-chlorobenzotrifluoride. The yield of crude product is 93.2%. The crude product was directly used in the next reaction without purification.

[0038] 2) Preparation of 2-chloro-6-trifluoromethylbenzenecyanide

[0039] 180g of 2-fluoro-3-chlorobenzotrifluoride was dissolved in 360mL of dry N,N-dimethylacetamide, the temperature was raised to 90°C, and 42.0g of sodium cyanide was slowly added in batches. After the addition, keep stirring at 90-100°C for 4 hours, and recover N,N-dimethylacetamide ...

Embodiment 2

[0046] 1) Preparation of 2-fluoro-3-chlorobenzotrifluoride

[0047] Add 215g of 2,3-dichlorobenzotrifluoride, 73g of potassium fluoride, 7g of triphenylphosphine bromide and 430mL of 1,3-dimethylimidazolidinone into a 1000mL three-necked flask equipped with a rectification column, and stir to raise the temperature Reflux reaction. After 1 hour of reaction, 185 g of a colorless transparent liquid began to evaporate slowly, and the content of GC analysis was 93.9%, which was 2-fluoro-3-chlorobenzotrifluoride. The yield of crude product is 93.2%. The crude product was directly used in the next reaction without purification.

[0048] 2) Preparation of 2-chloro-6-trifluoromethylbenzenecyanide

[0049] 180g of 2-fluoro-3-chlorobenzotrifluoride was dissolved in 360mL of dry N,N-dimethylacetamide, the temperature was raised to 90°C, and 42.0g of sodium cyanide was slowly added in batches. After the addition, keep stirring at 90-100°C for 4 hours, and recover N,N-dimethylacetamide ...

Embodiment 3

[0056] 1) Preparation of 2-fluoro-3-chlorobenzotrifluoride

[0057] Add 215g of 2,3-dichlorobenzotrifluoride, 83g of sodium fluoride, 10g of diisopropylethylamine and 400mL of N-methylpyrrolidone into a 1000mL three-necked flask equipped with a rectification column, stir and raise the temperature to reflux. After 4 hours of reaction, 183 g of a colorless transparent liquid began to evaporate slowly, and the content of GC analysis was 93.5%, which was 2-fluoro-3-chlorobenzotrifluoride. The yield of crude product is 92.2%. The crude product was directly used in the next reaction without purification.

[0058] 2) Preparation of 2-chloro-6-trifluoromethylbenzenecyanide

[0059] 180g of 2-fluoro-3-chlorobenzotrifluoride was dissolved in 360mL of dry dimethyl sulfoxide, the temperature was raised to 90°C, and 177.1g of potassium cyanide was slowly added in batches. After the addition, the reaction was refluxed for 2 hours. After vacuum distillation, the residue was dissolved in 9...

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Abstract

The invention discloses a synthesis method of 2-(trifluoromethyl) benzamide. The method comprises the following steps: by taking 2,3-dichlorobenzotrifluoride as a raw material, carrying out fluorination and cyano substitution to prepare 2-fluoro-6-cyano benzotrifluoride; and carrying out hydrogenation dechlorination and then hydrolysis on the 2-fluoro-6-cyano trifluorotoluene, or carrying out hydrolysis and then hydrogenation dechlorination on the 2-fluoro-6-cyano trifluorotoluene to prepare the 2-trifluoromethyl benzamide. The 2-trifluoromethyl benzamide is synthesized through simple reaction, and the method has the characteristics that the raw materials are cheap and easy to obtain, and an isomer of the intermediate 2-fluoro-3-chloro-trifluorotoluene does not participate in subsequent reaction and is easy to remove. In the steps, common flammable, explosive, highly toxic or difficult-to-preserve reagents in the existing synthesis method are not used, so that the harm to the environment and operators is avoided; meanwhile, the total yield of the product reaches 67% or above, and the purity is 97% or above.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a synthesis method of 2-trifluoromethylbenzamide. Background technique [0002] Organic compounds with trifluoromethylbenzamide structural units have good biological activity and are widely used in the fields of medicine, pesticides, synthetic dyes, etc., so they have broad application prospects. [0003] The synthesis of disclosed 2-trifluoromethylbenzamide mainly contains the following methods: [0004] Method 1, the patent publication No. US2008 / 86008 discloses the preparation of 2-trifluoromethylbenzamide by reacting o-trifluoromethylbenzoyl chloride with ammonia water as a raw material. [0005] Method 2: Bulletin des Societes Chimiques Belges, 1930, vol.39, p.298, 306, 307 reported that 2-trifluoromethylbenzoic acid was prepared from 2-trifluoromethylbenzoic acid by alkali hydrolysis, and 2-trifluoromethylbenzoic acid was prepared by esterification react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/65C07C231/06C07C231/12C07C255/50C07C253/30C07C253/14C07C25/13C07C17/20
CPCC07C231/065C07C231/12C07C253/30C07C253/14C07C17/208C07C233/65C07C255/50C07C25/13
Inventor 陈正伟征玉荣何彬张莉笋刘亮
Owner 内蒙古蓝科生物科技有限公司
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