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Synthetic process of difenoconazole

A difenoconazole and synthesis process technology, applied in the direction of organic chemistry, can solve the problems of pollution, high content of condensation reaction isomers, large amount of catalyst AICl3, etc., and achieve the effect of simple process and high product purity

Pending Publication Date: 2019-07-05
CHANGSHA XINBEN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing technology all has different shortcoming: in the acylation reaction, catalyst AICl3 consumption is big, is difficult to handle, and pollution is serious; Bromination reaction emits hydrogen bromide and pollutes environment, corrodes equipment; quality and yield

Method used

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  • Synthetic process of difenoconazole

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Acetylation reaction: Add 300 grams (Bmim) of Cl-FeCl3 ionic liquid to a 1000ml four-necked reaction flask with stirring, reflux condenser and thermometer, and add 147 grams (1.0mol) of m-dichlorobenzene and 94.2 grams of m-dichlorobenzene under stirring (1.2 mol) acetyl chloride, stirred and heated up, and kept at 50°C±2°C for 4 hours. After the reaction was completed, it was extracted with 200 ml×2 cyclohexane, the organic phase was combined, and the solvent was distilled off under reduced pressure to obtain liquid 2,4- Dichloroacetophenone 181.1 grams, purity 97.6%, yield 95.8%. The ionic liquid was washed with cyclohexane and dried for use.

[0020] Bromination reaction: add 300 milliliters of dichloromethane into 1000 milliliters of four-neck flasks with stirrer, thermometer, condenser and constant pressure titration funnel, add 189 grams of 2,4-dichloroacetophenone successively under stirring, 120 Milliliter of 27.5% hydrogen peroxide, 15 grams of sodium percarbo...

Embodiment 2

[0025] Acetylation reaction: Add 300 grams (Bmim) of Cl-FeCl3 ionic liquid to a 1000ml four-necked reaction flask with stirring, reflux condenser and thermometer, and add 147 grams (1.0mol) of m-dichlorobenzene and 94.2 grams of m-dichlorobenzene under stirring (1.2mol) acetyl chloride, stirred and heated up, and kept at 60°C ± 2°C for 4 hours. After the reaction, extracted twice with 200 ml cyclohexane, combined the organic phase, and evaporated the solvent under reduced pressure to obtain liquid 2,4 -Dichloroacetophenone 181.5 grams, content 96.9%, yield 96.0%. The ionic liquid was washed with cyclohexane and dried for use.

[0026] Bromination reaction: add 300 milliliters of dichloromethane into 1000 milliliters of four-neck flasks with stirrer, thermometer, condenser and constant pressure titration funnel, add 189 grams of 2,4-dichloroacetophenone successively under stirring, 150 Milliliter of 27.5% hydrogen peroxide, 15 grams of sodium percarbonate; then slowly add 80 g...

Embodiment 3

[0031] Acetylation reaction: Add 300 grams (Bmim) of Cl-FeCl3 ionic liquid to a 1000ml four-necked reaction flask with stirring, reflux condenser and thermometer, and add 147 grams (1.0mol) of m-dichlorobenzene and 94.2 grams of m-dichlorobenzene under stirring (1.2 mol) acetyl chloride, stirred and heated up, and kept at 40°C±2°C for 4 hours. After the reaction, extracted twice with 200 ml cyclohexane, combined the organic phase, and evaporated the solvent under reduced pressure to obtain liquid 2,4 -148.4 grams of dichloroacetophenone, content 93.1%, yield 78.5%. The ionic liquid was washed with cyclohexane and dried for use.

[0032] Bromination reaction: 300 milliliters of dichloromethane is added in 1000 milliliters four-neck flasks with stirrer, thermometer, condenser and constant pressure titration funnel, add 189 grams of 2,4-dichloroacetophenone under stirring, then in Slowly add 80 grams of bromine dropwise at room temperature (a large amount of hydrogen bromide gas...

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Abstract

The invention discloses a synthetic process of difenoconazole, comprising the steps of synthesizing 2,4-dichloroacetophenone through ionic liquid acylation using m-dichlorobenzene as a raw material; then synthesizing alpha-bromo-2,4-dichloroacetophenone through a green bromination method; subjecting the alpha-bromo-2,4-dichloroacetophenone and 1,2-propanediol to cyclization to generate a ketal compound that is 2-(2,4-dichlorophenyl)-2-bromomethyl-4-methyl-1,3-dioxolane; subjecting the ketal compound and 1,2,4-triazole potassium to condensation to generate 1-[[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole; and finally subjecting the 1-[[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole and parachlorophenol to etherification to obtain the difenoconazole. The process has advantages of easily available raw materials, a high reaction conversion ratio, few byproducts, capability of being friendly to production environment and a low cost.

Description

technical field [0001] The invention relates to fine chemical technology, in particular to a synthesis process of difenoconazole. Background technique [0002] Difenoconazole is an excellent variety of triazole fungicides, with broad-spectrum, high efficiency, low residue, long-lasting characteristics, and good systemic, fumigation and eradication effects. At present, the process adopted by most domestic production enterprises is to use m-dichlorobenzene as raw material, and through acylation reaction, bromination reaction, cyclization reaction, condensation reaction and etherification reaction, the crude product of difenoconazole is obtained, and the crude product is refined The finished product of difenoconazole was obtained. Existing technology all has different shortcoming: in the acylation reaction, catalyst AICl3 consumption is big, is difficult to handle, and pollution is serious; Bromination reaction emits hydrogen bromide and pollutes environment, corrodes equipmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06
CPCC07D405/06
Inventor 刘建李刚
Owner CHANGSHA XINBEN CHEM
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