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2-(4-phenoxyphenyl)oxirane and preparation method and application thereof

A technology of phenoxyphenyl and ethylene oxide, which is applied in the application field of preparing difenoconazole fungicide, can solve the problems of low difenoconazole crude product content and high isomer content, and achieve Novel preparation process, high product purity and good quality

Inactive Publication Date: 2012-05-02
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The content of the difenoconazole crude product obtained by the existing production technology is not high (80%-82%), mainly due to the high content of isomers (10%-15%)

Method used

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  • 2-(4-phenoxyphenyl)oxirane and preparation method and application thereof
  • 2-(4-phenoxyphenyl)oxirane and preparation method and application thereof
  • 2-(4-phenoxyphenyl)oxirane and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 2-[2-chloro-4-(4-chlorophenoxy)-phenyl]oxirane

[0037]

[0038] 0.098mol 2-bromo-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone, 50mL tetrahydrofuran, add 0.049mol sodium borohydride under ice bath, TLC monitoring complete reaction; add 50mL hydrogen Sodium oxide solution, TLC monitors complete reaction; add dilute hydrochloric acid to neutrality, dichloromethane extracts, combine organic layers, dry over anhydrous sodium sulfate, spin dry to give light yellow liquid 2-[2-chloro-4-(4-chloro Phenoxy)-phenyl]oxirane, yield 86.0%. 1 H NMR (CDCl 3 , 400MHz) δ: 2.67 (dd, J=2.4Hz, J=5.6Hz, 1H, CH2), 3.18 (dd, J=3.2Hz, J=5.6Hz, 1H, CH2) 2 ), 4.16 (dd, J=2.4Hz, 3.2Hz, 1H, CH), 6.87 (dd, J=2.4Hz, J=8.4Hz, 1H, C 6 h 3 5-H), 6.95(d, J=8.8Hz, 2H, C 6 h 4 2,6-H), 6.98 (d, J=2.4Hz, 1H, C 6 h 3 3-H), 7.18(d, J=8.4Hz, 1H, C 6 h 3 6-H), 7.31(d, J=8.8Hz, C 6 h 4 3,5-H).

Embodiment 2

[0040] Preparation of 2-[2-chloro-4-(4-chlorophenoxy)-phenyl]oxirane

[0041] 0.098mol 2-chloro-1-[2-chloro-4-(4-chlorophenoxy)phenyl]ethanone, 50mL tetrahydrofuran, add 0.049mol sodium borohydride under ice-cooling, TLC monitoring complete reaction; add 50mL hydrogen Sodium oxide solution, TLC monitors complete reaction; add dilute hydrochloric acid to neutrality, extract with dichloromethane, combine organic layers, dry over anhydrous sodium sulfate, spin dry to give light yellow liquid 2-[2-chloro-4-(4-chloro Phenoxy)-phenyl]oxirane, yield 85.0%.

Embodiment 3

[0043] Preparation of 2-[2-chloro-4-(4-chlorophenoxy)-phenyl]oxirane

[0044] 1.0mol 2-chloro-4-(4-chlorophenoxy)benzaldehyde, 1.2mol sulfur ylide and 150ml toluene and dimethyl sulfide, add 3.0mol KOH solution under control at 10°C, after adding, continue to stir for a while , add dilute hydrochloric acid to neutralize to neutrality, then separate the liquids, and spin the solvent to obtain 2-[2-chloro-4-(4-chlorophenoxy)-phenyl]oxirane with a yield of 90.0%.

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Abstract

The invention discloses 2-(4-phenoxyphenyl)oxirane shown as a formula III. X1 and X2 are H, CH3, CH3CH2, F3C, CH3O, NO2, CN, Cl, Br or F. The 2-(4-phenoxyphenyl)oxirane is prepared by a method (1) or (2) or (3) comprising the following steps of: (1) performing epoxidation reaction on sulfur ylide[(CH3)3S<+>CH3SO4<->] and 4-phenoxybenzaldehyde to obtain the 2-(4-phenoxyphenyl)oxirane; (2) reducing2-halo-1-(4-phenoxyphenyl)ethanone by using sodium borohydride to obtain 2-halo-1-(4-phenoxyphenyl)ethanol, and cyclizing in the presence of sodium hydroxide to obtain the 2-(4-phenoxyphenyl)oxirane;and (3) oxidizing 4-phenoxystyrene by using hydrogen peroxide or KHSO5 to obtain the 2-(4-phenoxyphenyl)oxirane. 2-[2-chloro-4-(4-chlorophenoxy)-phenyl]oxirane is applied to the preparation of a difenoconazole bactericide.

Description

technical field [0001] The present invention relates to a new compound and its preparation method and its application in the preparation of pesticide fungicides, specifically the synthesis of 2-(4-phenoxyphenyl)oxirane and its use in the preparation of difenoconazole fungicides in the application. Background technique [0002] Difenoconazole, also known as difenoconazole, is a triazole fungicide. Difenoconazole has systemic properties and is a sterol demethylation inhibitor with a broad bactericidal spectrum. Foliage treatment or seed treatment can improve the yield and quality of crops, and it is effective for Ascomycetes, Basidiomycetes and the genus Alternaria, Ascodiospora, Cercospora, Craniospora, Coccidioides, Deuteromycetes including Phoma, Septoria, Septoria, and Scutellaria, Erysiphaceae, Rusts, and certain species-borne pathogens have long-lasting protective and therapeutic activities. At present, the domestic market is becoming more and more mature. This produc...

Claims

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Application Information

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IPC IPC(8): C07D303/22C07D301/12C07D405/06
Inventor 胡艾希陈晓东唐建刚叶姣张明明
Owner HUNAN UNIV
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