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Method for synchronizing m-benzenyl trifluoride di-cyan acetonphenone

A technology of trifluoromethylbenzene and cyanoacetophenone, applied in the field of organic synthesis, can solve the problems of reduced production cost, high production cost, and high product yield, and achieve low production cost, easy recycling, and high product yield Effect

Active Publication Date: 2012-11-07
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the deficiencies of expensive raw materials, high production cost and low product yield in the prior art, the present invention provides an important intermediate m-trifluoromethylphenyl-p-cyanobenzene of semicarbazone insecticide metaflumizone The synthetic method of ethyl ketone adopts cheap 4-cyanobenzyl chloride to synthesize 4-cyanophenylacetonitrile instead of 4-methylbenzonitrile, reacts in a low-boiling solvent, simplifies the operation process, and the process of distilling off the solvent is relatively simple , so that the product yield is high and the production cost is reduced

Method used

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  • Method for synchronizing m-benzenyl trifluoride di-cyan acetonphenone

Examples

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Effect test

Embodiment 1

[0022] A kind of synthetic method of m-trifluoromethylbenzene-p-cyanoacetophenone is starting raw material with 4-cyanobenzyl chloride, and concrete steps comprise:

[0023] (1) Add 50 mL of water, 34.3 g of sodium cyanide aqueous solution (dissolving 10.29 g of pure sodium cyanide) and 3 g of catalyst benzyltriethylammonium chloride into a 500 mL four-necked flask equipped with a stirrer, a thermometer and a condenser (TEBAC). After sealing, start stirring while raising the temperature. When the temperature reaches 90-95°C, slowly add 29.73g of 4-cyanobenzyl chloride in toluene solution (121.2g in total) in about 1 hour, and keep reflux during the dropwise addition. Keep warm for 1.5 hours after feeding. After cooling, add 200 mL of water to wash once. The water layer was separated, and the organic layer was dried and then distilled under reduced pressure to obtain 28.82 g of a white solid, namely 4-cyanophenylacetonitrile, with a content of 96% and a yield of 97.4%;

[00...

Embodiment 2

[0027] A kind of synthetic method of m-trifluoromethylbenzene-p-cyanoacetophenone is starting raw material with 4-cyanobenzyl chloride, and concrete steps comprise:

[0028] (1) Add 50mL of water, 51.45g of sodium cyanide aqueous solution (dissolved with 10.29g of pure sodium cyanide) and 3g of catalyst benzyl triethyl chloride into a 500mL four-necked flask equipped with a stirrer, thermometer and condenser ammonium (TEBAC). After sealing, start stirring while raising the temperature. When the temperature reaches 90-95°C, slowly add 28.94g of 4-cyanobenzyl chloride in toluene solution (144.7g in total) in about 1 hour, and keep reflux during the dropwise addition. Keep warm for 1.5 hours after feeding. After cooling, add 200 mL of water to wash once. The water layer was separated, and the organic layer was dried and distilled under reduced pressure to obtain 28.75 g of a white solid with a content of 96.2% and a yield of 97.4%;

[0029] (2) Add 14.34g of 4-cyanophenylaceto...

Embodiment 3

[0032] A kind of synthetic method of m-trifluoromethylbenzene-p-cyanoacetophenone is starting raw material with 4-cyanobenzyl chloride, and concrete steps comprise:

[0033](1) Add 50 mL of water, 27.1 g of sodium cyanide aqueous solution (dissolving 10.29 g of pure sodium cyanide) and 3 g of catalyst benzyl triethyl chloride into a 500 mL four-necked flask equipped with a stirrer, a thermometer and a condenser. ammonium (TEBAC). After sealing, start stirring while raising the temperature. When the temperature reaches 90-95°C, slowly add 30.03g of 4-cyanobenzyl chloride in toluene solution (100.1g in total) in about 1 hour, and keep reflux during the dropwise addition. Keep warm for 1.5 hours after feeding. After cooling, add 200 mL of water to wash once. The water layer was separated, and the organic layer was dried and distilled under reduced pressure to obtain 28.68 g of a white solid with a content of 95.6% and a yield of 96.5%;

[0034] (2) Add 14.34g of 4-cyanophenyla...

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Abstract

The invention discloses a method for synchronizing m-benzenyl trifluoride di-cyan acetonephenone which is an important intermediate for metaflumizone, a kind of efficient insecticide. The method includes utilizing 4-cyanobenzylchloride as raw materials to generate 4-cyano phenylacetonitrile to be reacted with methyl 3-benzoate in organic solvent for 5-8 hours. The yield of the intermediate of the metaflumizone produced by the method is higher than 90%, and content is higher than 89%. The method for synchronizing m-benzenyl trifluoride di-cyan acetonphenone is high in yield, low in cost and can be used for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing an important intermediate m-trifluoromethylbenzene-p-cyanoacetophenone of semicarbazone insecticide metaflumizone. technical background [0002] Metaflumizone (BAS320I) is a brand-new compound jointly developed by German BASF and Japanese pesticide company, which belongs to semicarbazone insecticides. Metaflumizone has a unique mechanism of action, has insecticidal activity itself, does not require biological activation, and has no cross-resistance with existing various insecticides. Metaflumizone can effectively control Lepidoptera pests and some Coleoptera larvae and adults in various places, and can also be used to control ants, termites, flies, cicadas and other pests. [0003] m-trifluoromethylbenzene-p-cyanoacetophenone is an important intermediate in the synthesis of metaflumizone and an important raw material for the preparation of crop...

Claims

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Application Information

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IPC IPC(8): C07C255/56C07C253/30
Inventor 刘龙飞史庆苓马韵升栾波吴文雷高洪奎
Owner JINGBO AGROCHEM TECH CO LTD
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