Synthesis method of acaricide cyflumetofen intermediate p-tert-butyl phenylacetonitrile

A technology of tert-butylphenylacetonitrile and cyflufen, which is applied in the field of pesticides and pharmaceuticals, can solve the problems of high and serious distillation residues, environmental pollution, etc., and achieve the effects of high reaction yield, short steps and few side reactions

Inactive Publication Date: 2018-12-21
SHANDONG ACADEMY OF PESTICIDE SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The technical effect of this new technology compared to previous methods has been that it produces fewer unwanted byproducts during production while still producing good results for certain applications such as medicine or chemicals.

Problems solved by technology

This patented technical problem addressed in this patents relates to how to efficiently produce pure chemical compounds called cyclofluens that are effective for controlling insect populations without causing harmful side effectes such as pesticidal activity against other living things like humans.

Method used

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  • Synthesis method of acaricide cyflumetofen intermediate p-tert-butyl phenylacetonitrile
  • Synthesis method of acaricide cyflumetofen intermediate p-tert-butyl phenylacetonitrile

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Embodiment 1

[0028] The synthetic method of tert-butylphenylacetonitrile of acaricide cyflumetate intermediate, comprises the following steps:

[0029] 1) Under the condition of argon, mix ethyl cyanoacetate, potassium tert-butoxide and tert-butanol, raise the temperature to 98°C, control the pressure to 4.5 atmospheres, and mix 1mol of tert-butylchlorobenzene and DMSO within 30min The solution was added in 3 batches, then the reaction temperature was controlled to be 112°C, the reaction pressure was 5 atmospheres, the reaction was completed for 2.5 hours, then deionized water was added, the reaction temperature was controlled to be 142°C, the reaction pressure was 8 atmospheres, and the reaction was continued for 5 hours Finish;

[0030] The molar ratio of 4-tert-butylchlorobenzene to ethyl cyanoacetate is 1:1.35, the molar ratio of ethyl cyanoacetate to potassium tert-butoxide is 1:1.55, and the molar ratio of ethyl cyanoacetate to tert-butanol 1g:10ml, the ratio of 4-tert-butylchlorobe...

Embodiment 2

[0033] The synthetic method of tert-butylphenylacetonitrile of acaricide cyflumetate intermediate, comprises the following steps:

[0034] 1) Under nitrogen, mix methyl cyanoacetate, sodium tert-butoxide, and tetrahydrofuran, heat up to 80°C, control the pressure to 3 atmospheres, and divide 1mol of tert-butylbromobenzene and DMF solution within 20min Add in 3 batches, then control the reaction temperature to 95°C, the reaction pressure to 4 atmospheres, and finish the reaction for 1 hour, then add deionized water, control the reaction temperature to 130°C, and the reaction pressure to 6 atmospheres, and continue the reaction for 4 hours to end;

[0035] The molar ratio of 4-tert-butylbromobenzene to methyl cyanoacetate is 1:1.2, the molar ratio of methyl cyanoacetate to sodium tert-butoxide is 1:1.4, and the molar ratio of methyl cyanoacetate to tetrahydrofuran is 1g : 8ml, the consumption ratio of 4-tert-butylbromobenzene and DMF is 1g: 4ml, and the consumption ratio of sodi...

Embodiment 3

[0038] The synthetic method of tert-butylphenylacetonitrile of acaricide cyflumetate intermediate, comprises the following steps:

[0039] 1) Under argon atmosphere, mix isopropyl cyanoacetate, potassium tert-butoxide and tert-butanol, heat up to 105°C, control the pressure to 5 atmospheres, and mix 1mol of tert-butyl iodobenzene and Add the DMSO solution in 3 batches, then control the reaction temperature to 120°C, the reaction pressure to 7 atmospheres, and the reaction is over for 3 hours, then add deionized water, control the reaction temperature to 150°C, and the reaction pressure to 9 atmospheres, and continue the reaction for 6 hours Finish;

[0040] The consumption ratio of 4-tert-butyl iodobenzene and isopropyl cyanoacetate is a molar ratio of 1:1.45, the consumption of isopropyl cyanoacetate and organic base is a molar ratio of 1:1.62, and the consumption ratio of isopropyl cyanoacetate and DMSO is 1g:12ml, the ratio of 4-tert-butyl iodobenzene to DMSO is 1g:6ml, an...

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Abstract

The invention discloses a synthesis method of an acaricide cyflumetofen intermediate p-tert-butyl phenylacetonitrile, and belongs to the field of pesticide preparation. The synthesis method is characterized in that a reaction is performed on 4-tert-butyl halobenzene and cyanoacetate to obtain the p-tert-butyl phenylacetonitrile. A reaction process comprises the following steps: 1), under a protective gas condition, uniformly mixing the cyanoacetate, organic alkali and a solvent A, raising the temperature to 80-105 DEG C, controlling the pressure to be 3-5 atmospheric pressures, adding a solution of the tert-butyl halobenzene and a solvent B in three batches within 20-40 min, then controlling the reaction temperature to be 95-120 DEG C, controlling the reaction pressure to be 4-7 atmospheric pressures, carrying out a reaction for 1-3 hours, then adding deionized water, controlling the reaction temperature to be 130-150 DEG C, controlling the reaction pressure to be 6-9 atmospheric pressures, and continuing the reaction for 4-6 hours; 2), removing the solvents from a system by using a rotary evaporator, then transferring a remainder to water, adding a solvent C, stirring, layering, collecting an organic phase, drying by using a drying agent, then filtering, collecting a filtrate, distilling the filtrate under reduced pressure, and collecting a fraction with the temperature of 78-79 DEG C (0.1 torr) to obtain the p-tert-butyl phenylacetonitrile. According to the synthesis method, the steps are few, the yield is relatively high and the pollutant emission is less.

Description

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Claims

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Application Information

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Owner SHANDONG ACADEMY OF PESTICIDE SCI
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