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Preparation process of oxime strain ester

A technology of trifloxystrobin and ketoxime, which is applied in the field of preparation of organic compounds, can solve the problem of not providing a synthesis process, etc., and achieves the effects of mild operating conditions, reduction of waste water discharge, and avoidance of esterification

Inactive Publication Date: 2005-01-05
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Literature J.Chem.Soc., 1965:5298, Tetrahedron Lett., 1980, 21:4957.J.Org.Chem., 1981,46(1):211, EP0363818A1, US5041618, Angew.Chem., 1959,71 : 349, US5194662 and CN1109686 provide the partial synthesis of trifloxystrobin and intermediates, but do not provide a complete synthetic process

Method used

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  • Preparation process of oxime strain ester

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Embodiment 1

[0019] Synthesis of 2-(2'-methylphenyl)-2-oxoacetic acid

[0020] Add 2ml (0.015mol) of o-methyl acetophenone, 6g of sodium hydroxide, and 200ml of water into a 500ml round bottom flask, and add 7g of potassium permanganate into the flask in batches under stirring in an ice-water bath. When the last batch of potassium permanganate is added, the color in the reaction system remains unchanged for 1 hour. After the reaction is completed, add sodium bisulfite solution dropwise to make the purple color of the mixed solution fade away, and remove the manganese dioxide solid by suction filtration. Ether extraction removed unreacted starting material. The aqueous phase was acidified to pH=4 with concentrated hydrochloric acid, a white solid appeared, extracted with 2 x 50ml ether, and the white solid was dissolved in ether. The collected organic phase was dried with anhydrous magnesium sulfate, and diethyl ether was evaporated to obtain 2 g of yellow 2-(2'-methylphenyl)-2-oxoacetic a...

Embodiment 2

[0041] Other steps carry out embodiment 1 repeatedly in the same steps, but wherein the synthesis of 2-(2'-bromomethylphenyl)-2-oxomethyl acetate of the 3rd step is carried out according to the following steps: 1g (0.006mol) -(2'-methylphenyl)-2-oxoacetic acid methyl ester was dissolved in 20ml of carbon tetrachloride and placed in a 100ml three-necked flask, and 1.5g (0.012mol) of NBS (N-bromosuccinimide) was added and 0.2gBPO (benzoyl peroxide), irradiated with a 250W mercury lamp. During the reaction, TLC (ethyl acetate:petroleum ether=1:8) was used to track the progress of the reaction, and TLC showed that the raw material point basically disappeared to end the reaction. The solution was washed once with 50ml water, saturated sodium bicarbonate (NaHCO 3 ) solution for three washes. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a yellow-brown product. Purified by silica gel column chromatography (ethyl acetate:p...

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Abstract

The invention discloses a trifloxystrobin preparing method, including the steps as follows: (a) using ortho-methyl hypnone as raw material and using potassium permanganate to oxidize so as to obtain 2-(2'-methyl-phenyl)-2-carbonyl acetic acid; (b) making the product in step (a) react with methanol to obtain 2-(2'-methyl-phenyl)-2-carbonyl methyl acetate; (c) bromizing the product in step (b) to obtain 2-(2'-bromomethyl-phenyl)-2-carbonyl methyl acetate; (d) making the product in step (c) react with methoxy amine to obtain (E)-2-(2'-bromomethyl-phenyl)-2-carbonyl methyl acetate-O-methyl ketone oxime; (e) making the product in step (d) react with meta-trifluoromethyl hypnone oxime to obtain the product trifloxystrobin. It reduces the discharge of large amount of waste water in course of oxidization reaction, avoids esterification by adopting methyl- chloroformate, most operating conditions are moderate.

Description

Technical field [0001] The present invention relates to a method for preparing organic compounds as pesticides, and in particular to a kind of trifloxystrobin ((E, E)-2-[1'-(3'-trifluoromethylphenyl)-ethyl-ylidene). Synthetic method of amine-oxy-tolyl]-2-carbonylacetic acid methyl ester-O-methyl ketoxime). Background technique [0002] Trifloxystrobin broad-spectrum fungicides are a new class of fluorinated fungicides successfully developed from the natural product Strobilurins as lead fungicide compounds. Its characteristics are: high efficiency, broad spectrum, protection, treatment, eradication, penetration, systemic activity, resistance to rain erosion, and long duration of effect. It is effective against strains resistant to 1,4-demethylase inhibitors, benzamides, dicarboxamides and benzimidazole, and has no cross-resistance with existing fungicides. It has good activity against almost all fungal diseases (Ascomycetes, Basidiomycetes, Oomycetes and Deuteromycetes) suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/48
Inventor 朱志良张荣华袁莉莉倪亚明
Owner TONGJI UNIV
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