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Green synthesis method of 3,4,5-trifluorobromobenzene

A technology of green synthesis and trifluorobromobenzene, which is applied in 3 fields, can solve the problems of increased production cost, large amount of saline wastewater, and low utilization rate of bromine, and achieve the effects of reduced production cost, high purity, and improved utilization rate

Inactive Publication Date: 2021-04-09
SHANGYU XIES CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen from the above-mentioned prior art that although the target product with higher purity and yield can be obtained in the current synthetic method, a large amount of sodium nitrite will be used as a diazotization reagent in the production, and a large amount of saline waste water will be produced. , and the utilization rate of bromine is low, which greatly increases the preparation cost of the product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Add 13g of 2,3,4-trifluoroaniline and 100ml of water into the reactor, then add 18g of hydrobromic acid and 5g of 0.1mol / L hydrogen peroxide, mix and react for 0.5h at 3°C, and prepare 2,3,4-trifluoro-6-bromoaniline was obtained;

[0028] (2) 8g nitrosylsulfuric acid and 25ml 60wt% sulfuric acid solution are mixed to make the sulfuric acid solution of nitrosylsulfuric acid, in the above-mentioned 2,3,4-trifluoro-6-bromoaniline, add 0.55ml Add the sulfuric acid solution of nitrosylsulfuric acid at a dropping rate of / min, and react for 1 hour at 2°C to obtain a diazonium salt solution;

[0029] (3) Add 10 g of sodium hypophosphite and 0.8 g of copper oxide supported by a porous material as a catalyst to the diazonium salt solution prepared above, first add sodium hypophosphite and the catalyst at -5°C, stir and mix for 3 hours, and then mix with 0.5 The heating rate of ℃ / min is raised to 5 ℃, and the reaction is kept for 30 minutes. Finally, the temperature is raise...

Embodiment 2

[0031] (1) Add 16g of 2,3,4-trifluoroaniline and 100ml of water into the reactor, then add 22g of hydrobromic acid and 5g of 0.1mol / L hydrogen peroxide, mix and react for 1.5h at 5°C, and prepare 2,3,4-trifluoro-6-bromoaniline was obtained;

[0032] (2) 8g nitrosylsulfuric acid and 25ml 60wt% sulfuric acid solution are mixed to make the sulfuric acid solution of nitrosylsulfuric acid, in the above-mentioned 2,3,4-trifluoro-6-bromoaniline, add 1.05ml Add the sulfuric acid solution of nitrosylsulfuric acid at a dropping rate of / min, and react for 1 hour at 7°C to obtain a diazonium salt solution;

[0033] (3) Add 10 g of sodium hypophosphite and 1.5 g of copper oxide supported by a porous material as a catalyst to the diazonium salt solution prepared above, first add sodium hypophosphite and the catalyst at 0 ° C, stir and mix for 5 h, and then Raise the temperature to 5°C at a heating rate of 1°C / min, keep the temperature for 30 minutes, and finally raise the temperature to 1...

Embodiment 3

[0035] (1) Add 14g of 2,3,4-trifluoroaniline and 100ml of water into the reactor, then add 19g of hydrobromic acid and 5g of 0.1mol / L hydrogen peroxide, mix and react for 1 hour at 4°C, and obtain 2,3,4-Trifluoro-6-bromoaniline;

[0036] (2) 8g nitrosylsulfuric acid and 25ml 60wt% sulfuric acid solution are mixed to obtain the sulfuric acid solution of nitrosylsulfuric acid, in the above-mentioned 2,3,4-trifluoro-6-bromoaniline, add 0.75ml Add the sulfuric acid solution of nitrosylsulfuric acid at a dropping rate of / min, and react for 1 hour at 5°C to obtain a diazonium salt solution;

[0037] (3) Add 10 g of sodium hypophosphite and 1 g of copper oxide supported by a porous material to the diazonium salt solution prepared above as a catalyst, first add sodium hypophosphite and the catalyst at -5 ° C, stir and mix for 3.5 h, and then mix with 0.5 The heating rate of ℃ / min is raised to 5 ℃, and the reaction is kept for 30 minutes. Finally, the temperature is raised to 15 ℃ at a...

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Abstract

The invention discloses a green synthesis method of 3,4,5-trifluorobromobenzene. The green synthesis method comprises the following steps: adding 2,3,4-trifluoroaniline and water into a reactor, adding hydrobromic acid and hydrogen peroxide, and carrying out a hybrid reaction to obtain 2,3,4-trifluoro-6-bromoaniline after the reaction is ended; slowly adding a sulfuric acid solution of nitroso sulfuric acid into the prepared 2,3,4-trifluoro-6-bromoaniline, and carrying out a diazotization reaction to obtain a diazonium salt solution; and adding sodium hypophosphite and porous material-loaded copper oxide into the prepared diazonium salt solution as catalysts, conducting reacting, and sequentially carrying out distillation, alkali washing, water washing and reduced-pressure rectification on reaction liquid after the reaction is finished so as to obtain a target product. According to the method, nitrososulfuric acid replaces sodium nitrite to serve as a diazotization reagent, so no high-salt wastewater is discharged, production cost is reduced, and the method is more environmentally friendly; and hydrobromic acid serves as a bromine source, and hydrogen peroxide is added, so the utilization rate of bromine atoms is high, the adding amount of hydrobromic acid is reduced, and the amount of three wastes generated in implementation of the method is remarkably reduced.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a green synthesis method of 3,4,5-trifluorobromobenzene. Background technique [0002] 3,4,5-Trifluorobromobenzene is an important pesticide intermediate, mainly used in the synthesis of succinate dehydrogenase inhibitor fungicide flufenapyramide. Flufenapyramide is a highly selective pyrazole amide fungicide developed by BASF. It has a novel structure, broad spectrum and high efficiency, and its mode of action is different from existing fungicides. It has become a new hot spot in fungicide research. At the same time, 3,4,5-trifluorobromobenzene is also an important liquid crystal intermediate, which is used to produce the fourth generation TFT color liquid crystal material. [0003] There are few domestic research reports on 3,4,5-trifluorobromobenzene. The commonly used synthetic routes are as follows: 1. Use 2,3,4-trifluoroaniline as raw material to obtain 3,4,5-tr...

Claims

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Application Information

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IPC IPC(8): C07C17/093C07C25/13C07C245/20B01J23/72B01J35/10
CPCC07C17/093C07C245/20B01J23/72B01J35/60C07C25/13
Inventor 解卫宇陈少君顾林江卢晓健贺承相陈坚康
Owner SHANGYU XIES CHEM IND
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