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Preparation method of 2-nitryl-4-trifluoromethyl benzonitrile

A technology of trifluoromethylbenzonitrile and chlorobenzonitrile, which is applied in the field of preparation of 2-nitro-4-trifluoromethylbenzonitrile, and can solve the problems of expensive raw materials, high price, and poor yield , to achieve the effect of reducing production costs, reducing enterprise costs, and reducing process costs

Active Publication Date: 2017-05-10
PAPANNA BEIJING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Adopt 4-fluoro-3-nitrobenzobenzonitrile as raw material to prepare 2-nitro-4-trifluoromethylbenzonitrile in CN1359372A, the conversion rate of reaction, selectivity, productive rate are very poor, and raw material price is expensive, Not suitable for industrial production at all
However, cuprous cyanide is not only expensive, but also as a highly toxic reagent, there is great danger to operators and the environment, and industrialization is relatively difficult

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation method of 2-nitro-4-trifluoromethyl benzonitrile, comprises the steps:

[0030] (1) Under nitrogen protection, take cuprous cyanide (9g, 0.1mol, 0.1eq), sodium ferrocyanide (51g, 0.17mol, 0.17eq), 4-chloro-3-nitrotrifluorotoluene (225.6 g, 1 mol, 1 eq), sodium bromide (10.3 g, 0.1 mol, 0.1 eq) was placed in a reaction flask, 400 mL of anhydrous DMAC was added, the temperature was raised to an internal temperature of 160 °C, and the reaction was stirred for 6 hours. rate>99%, stop the reaction, filter the reaction system, and directly apply the residue for the second time;

[0031] (2) The filtrate was distilled under reduced pressure, and 195 g of fractions at 150-154° C. / 18 mmHg were collected, the yield was 90.5%, and the purity was 98.2%.

Embodiment 2

[0033] The preparation method of 2-nitro-4-trifluoromethyl benzonitrile, comprises the steps:

[0034] (1) Under nitrogen protection, 400 mL of anhydrous DMAC, sodium ferrocyanide (51 g, 0.17 mol, 0.17 eq), 4-chloro-3-nitrotrifluorotoluene, and 400 mL of anhydrous DMAC were added directly to the filtered solid after the reaction in Example 1. (225.6g, 1mol, 1eq) in a reaction flask, heat up to an internal temperature of 160°C, stir for 6 hours, take samples for liquid phase detection, the conversion of raw materials is >99%, stop the reaction, filter the reaction system, and filter the residue for the first step. Apply three times;

[0035] (2) Distilling the filtrate under reduced pressure, collecting 193 g of fractions at 150-154° C. / 18 mmHg, the yield is 90%, and the purity is 97.5%.

Embodiment 3

[0037] The preparation method of 2-nitro-4-trifluoromethyl benzonitrile, comprises the steps:

[0038] (1) Under nitrogen protection, 400 mL of anhydrous DMAC, sodium ferrocyanide (51 g, 0.17 mol, 0.17 eq), 4-chloro-3-nitrotrifluorotoluene, and 4-chloro-3-nitrotrifluorotoluene were directly added to the filtered solid after the reaction in Example 2. (225.6g, 1mol, 1eq) in a reaction flask, heat up to an internal temperature of 160°C, stir and react for 6 hours, take samples for liquid phase detection, the conversion rate of raw materials is >99%, stop the reaction, and filter the reaction system;

[0039] (2) Distilling the filtrate under reduced pressure, collecting 190 g of fractions at 150-154° C. / 18 mmHg, the yield is 88%, and the purity is 97%.

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PUM

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-nitryl-4-trifluoromethyl benzonitrile. According to the method, 3-nitryl-4-chlorobenzotrifluoride and cyaniding reagents, as raw materials, react with each other under the action of metal bromides and cuprous cyanide to obtain the 2-nitryl-4-trifluoromethyl benzonitrile. The cyaniding reagents are selected from at least one type of ferrous cyanides. The preparation method has the advantages that the metal bromides, which are low in price and easy to get, serve as activating agents, the cuprous cyanide serves as a catalyst, catalysis yield same as nickel bromide can be achieved, and production cost of enterprises can be reduced remarkably; non-toxicity of reaction reagents can be realized through cyanation based on the almost poisonless ferrous cyanides, environment protection requirements can be met, and industrialization can be realized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of 2-nitro-4-trifluoromethyl benzonitrile. Background technique [0002] 2-Nitro-4-trifluoromethyl benzonitrile is a special aromatic fluorine compound, which is an intermediate of various compounds such as medicine and pesticide. In terms of medicine, it is an intermediate for the synthesis of drugs for the treatment of hypoglycemia, analgesia, and blood pressure; In terms of pesticides, it is a high-efficiency, low-toxicity, low-dose pesticide intermediate, and 2-nitro-4-trifluoromethyl benzonitrile can be used to prepare enol derivatives as herbicides (isoxaflutole, sulfonylurea pyrazole, etc.), the control effect on weeds with drug resistance is particularly good; the herbicide synthesized by introducing trifluoromethyl into the aromatic ring is a hormonal selective post-emergence herbicide, specially used for the control of broad-leaved weeds ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/14C07C255/50
CPCC07C253/14C07C255/50
Inventor 陈安军孙飞杨文龙徐格邹晨
Owner PAPANNA BEIJING TECH
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