Preparation method for 2-nitro-4-trifluoromethyl cyanobenzene

A technology of trifluoromethylbenzonitrile and halotrifluorotoluene, applied in the field of preparation of 2-nitro-4-trifluoromethylbenzonitrile, can solve the problems of unsuitable large-scale industrial production, sodium cyanide and Potassium cyanide is highly toxic and potassium ferrocyanide has poor solubility, achieving the effect of low price, low toxicity and not easy to be poisoned

Active Publication Date: 2014-10-15
ZHEJIANG UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0002] 2-nitro-4-trifluoromethylbenzonitrile is a yellow crystal, which is a key intermediate in the synthesis of isoxazole herbicides. As reported in patent EP1000929, it provides a method using 3-nitro-4 - Fluorobenzotrifluoride is used as raw material, and potassium cyanide or sodium cyanide is used as cyanation reagent. Although no metal catalyst is needed in the reaction, the yield of reaction is low, and the sodium cyanide and potassium cyanide toxicity used are very high. big, dangerous
However, cuprous cyanide is a metal cyanide, which is highly toxic and has low solubility in organic media, and the amount used is greater than or equal to equimolar amounts, so it is not suitable for large-scale industrial prod

Method used

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  • Preparation method for 2-nitro-4-trifluoromethyl cyanobenzene
  • Preparation method for 2-nitro-4-trifluoromethyl cyanobenzene

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Experimental program
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Effect test

Embodiment 1

[0034] Add 1mmol of cuprous iodide, 1mmol of 3-nitro-4-chlorobenzotrifluoride, 1.5mmol of phenylacetonitrile, 2ml of N,N-dimethylformamide into a 10ml reaction flask, stir and heat to 160°C under air, after 18 hours Stop responding. 50 microliters of the reaction solution was extracted with water and dichloromethane, and the organic phase was taken for gas chromatography analysis. The result showed that the reaction yield was 53%.

Embodiment 2

[0036] Add 1mmol of cuprous bromide, 1mmol of 3-nitro-4-chlorobenzotrifluoride, 1.5mmol of phenylacetonitrile, 2ml of N,N-dimethylformamide into a 10ml reaction flask, stir and heat to 160°C under air, after 18 hours Stop responding. 50 microliters of the reaction solution was extracted with water and dichloromethane, and the organic phase was taken for gas chromatography analysis. The result showed that the reaction yield was 38%.

Embodiment 3

[0038] Add 1mmol cuprous iodide, 1mmol 3-nitro-4-chlorobenzotrifluoride, 1.5mmol phenylacetonitrile, 2mN-methylpyrrolidone into a 10ml reaction flask, stir and heat to 160°C under air, and stop the reaction after 18 hours. 50 microliters of the reaction solution was extracted with water and dichloromethane, and the organic phase was taken for gas chromatography analysis. The result showed that the reaction yield was 67%.

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Abstract

The invention provides a preparation method for 2-nitro-4-trifluoromethyl cyanobenzene. Under the catalysis of a metal catalyst, heating 3-nitro-4-halogen benzotrifluoride shown in the structural formula (2) and an organic cyanogen source in a solvent for reaction to obtain the 2-nitro-4-trifluoromethyl cyanobenzene shown in the structural formula (1), and the structural formula (2) and the structural formula (1) of 3-nitro-4-halogen benzotrifluoride and 2-nitro-4-trifluoromethyl cyanobenzene refer to the Specification. According to the invention, cheap copper salt or cuprous salt is used as the catalyst, and the method has the advantages of high conversion rate, relative low toxicity of a cyanation reagent, the capability of reaction under the atmosphere, and the like.

Description

technical field [0001] The invention relates to a preparation of benzonitrile compounds, in particular to a preparation method of 2-nitro-4-trifluoromethyl benzonitrile. Background technique [0002] 2-nitro-4-trifluoromethylbenzonitrile is a yellow crystal, which is a key intermediate in the synthesis of isoxazole herbicides. As reported in patent EP1000929, it provides a method using 3-nitro-4 - Fluorobenzotrifluoride is used as raw material, and potassium cyanide or sodium cyanide is used as cyanation reagent. Although no metal catalyst is needed in the reaction, the yield of reaction is low, and the sodium cyanide and potassium cyanide toxicity used are very high. Larger, more dangerous. [0003] The patent US4886936 uses cuprous cyanide as the cyanide source and 3-nitro-4-bromobenzonitrile as the raw material to obtain 2-nitro-4-trifluoromethylbenzonitrile with high conversion rate and selectivity . However, cuprous cyanide is a metal cyanide, which is highly toxic a...

Claims

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Application Information

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IPC IPC(8): C07C255/50C07C253/30
Inventor 吕萍王彦广金积松温俏东
Owner ZHEJIANG UNIV
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