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Method for synthesizing 2-Bromobenzotrifluoride

A technology of o-bromotrifluorotoluene and o-aminotrifluorotoluene is applied in the synthesis field of o-bromotrifluorotoluene, can solve the problems of many meta- and para-isomers, expensive raw materials, many impurities, etc. And the effect of less para-isomer, low production cost and high product content

Active Publication Date: 2017-01-18
苏州正济药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] For example, Chemical Communications 51(27), 5967-5970; 2015 and EP700885 reported the method of bromobenzene directly reacting with trifluoromethylation reagents, but the yield of this method is low, there are many meta-position and para-position isomers, and separation is difficult
[0004] Chemistry-A European Journal, 19(52), 17692-17697; 2013 reported the method for the synthesis of o-bromobenzotrifluorotoluene by reacting trifluoromethylating reagents such as o-bromoiodobenzene and ethyl trifluoropyruvate, but the route raw material Expensive, unable to meet the technological requirements of large-scale industrial production
[0005] Journal of Organic Chemistry, 78(22), 11126-11146; 2013 reported a method for synthesizing o-bromobenzotrifluoride with o-bromoiodobenzene and trifluoromethane or trifluoromethyl ketone, which is also expensive in raw materials
[0006] Journal of Fluorine Chemistry, 47 (2), 283-99; 1990 reported the method for the synthesis of 2-bromobenzotrifluoride with bromobenzene directly and trifluoromethyliron reaction, this method yield is low, and impurity is many, is not suitable for a large amount Production

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  • Method for synthesizing 2-Bromobenzotrifluoride

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preparation example Construction

[0024] The invention provides a kind of synthetic method of o-bromobenzotrifluoride, comprising the following steps:

[0025] A) o-aminotrifluorotoluene, hydrobromic acid and sodium nitrite are mixed and reacted to obtain a diazonium salt solution;

[0026] B) Mixing and reacting the above diazonium salt solution with cuprous bromide and hydrobromic acid to obtain o-bromobenzotrifluoride.

[0027] The reaction formula is as follows:

[0028]

[0029] The present invention overcomes the defects of the prior art such as high cost and many impurities in the product, adopts cheap and easy-to-obtain raw materials, has good solvent recovery effect, high yield and high product content, and synthesizes o-bromotrifluorotoluene in one step. Compared with other routes, intermediate There are few position and para isomers, and the production cost is low.

[0030] Specifically, the sodium nitrite solution is added dropwise to the mixed solution of o-aminotrifluorotoluene and hydrobrom...

Embodiment 1

[0046] Add 120g of o-aminobenzotrifluoride and 500ml of 48% hydrobromic acid into a 1000ml four-necked reaction flask, cool down to below -5°C, add dropwise a solution of 54g of sodium nitrite and 100ml of water, the dropping temperature is -5~0°C, Stirring was continued for 15 minutes after dropping. A solution of the diazonium salt was obtained.

[0047] Add 64g of cuprous bromide and 200ml of 48% hydrobromic acid to a 1L four-necked reaction flask equipped with mechanical stirring, a thermometer and a distillation device, heat to reflux, and add the diazonium salt solution prepared above dropwise. While carrying out atmospheric distillation, keep the rate of addition equal to the distillation rate, and collect the evaporated liquid until the evaporated liquid is no longer turbid.

[0048] Add 400ml of dichloromethane to the evaporated liquid for extraction, wash the organic layer with 300ml of water for 3 times, and wash with 300ml of 1mol / L sodium hydroxide solution for 1...

Embodiment 2

[0053] Add 120g of o-aminobenzotrifluoride and 360ml of 48% hydrobromic acid into a 1000ml four-necked reaction flask, cool down to below -5°C, add dropwise a solution of 62g of sodium nitrite and 100ml of water, the dropping temperature is 0-5°C, dropwise Continue stirring for 15 minutes after completion. A solution of the diazonium salt was obtained.

[0054] Add 75g of cuprous bromide and 340ml of 48% hydrobromic acid to a 1L four-necked reaction flask equipped with a mechanical stirrer, a thermometer, and a distillation device, heat to reflux, and add the diazonium salt solution prepared above dropwise. While carrying out atmospheric distillation, keep the rate of addition equal to the distillation rate, and collect the evaporated liquid until the evaporated liquid is no longer turbid.

[0055] Add 400ml of dichloromethane to the evaporated liquid for extraction, wash the organic layer with 300ml of water for 3 times, and wash with 300ml of 1mol / L sodium hydroxide solutio...

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Abstract

The present invention provides a method for synthesizing 2-Bromobenzotrifluoride, and the method comprises the following steps: A) 2-Aminotrifluoromethylbenzene, hydrobromic acid and sodium nitrite are mixed for reaction to obtain a diazonium salt solution; and B) the diazonium salt solution, cuprous bromide and hydrobromic acid are mixed for reaction to obtain the 2-Bromobenzotrifluoride. The method overcomes the defects of high cost, many product impurities and the like in prior art, cheap and accessible raw materials are used, solvent recovery effect is good, yield is high, product content is high, the 2-Bromobenzotrifluoride can be synthesized in one step, compared with other routes, meta and para isomers are less, and the production cost is low.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a synthesis method of o-bromobenzotrifluoride. Background technique [0002] O-Bromobenzotrifluoride is an important pesticide and pharmaceutical intermediate. The synthesis methods of o-bromotrifluorotoluene reported so far are not suitable for industrial production. [0003] For example, Chemical Communications 51(27), 5967-5970; 2015 and EP700885 reported the method of bromobenzene directly reacting with trifluoromethylation reagents, but the yield of this method is low, there are many meta-position and para-position isomers, and separation is difficult . [0004] Chemistry-A European Journal, 19(52), 17692-17697; 2013 reported the method for the synthesis of o-bromobenzotrifluorotoluene by reacting trifluoromethylating reagents such as o-bromoiodobenzene and ethyl trifluoropyruvate, but the route raw material It is expensive and cannot meet the process requiremen...

Claims

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Application Information

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IPC IPC(8): C07C17/093C07C25/13
CPCC07C17/093C07C245/20C07C25/13
Inventor 陆晓孙光福杨晓栋葛惠炯甘立新
Owner 苏州正济药业有限公司