Preparation method of kresoxim-methyl

A kresoxim-methyl and compound technology, which is applied in the direction of ether preparation, carboxylic acid ester preparation, and ester reaction to prepare ether, etc., can solve the problems of many side reactions, high equipment requirements, low product purity and yield, etc. Elimination of side reactions, elimination of side reactions, and easy-to-react effects

Active Publication Date: 2021-02-26
XINFA PHARMA
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0014] The raw material 2-(2-methylphenoxymethyl)benzoyl cyanide in the above-mentioned synthetic route 2 is expensive; and the preparation uses highly toxic sodium cyanide and thionyl chloride, which is not conducive to safety and environmental protection; feed hydrochloric acid gas, High requirements on equipment, serious corrosion, difficult to operate, not conducive to industrial scale-up
[0015] In summary, the existing preparation technology of kresoxim-methyl has disadvantages such as many steps, cumbersome operation, large amount of three wastes, non-environmental protection, high cost, many side reactions, low product purity and yield, so the design of a simple step, The synthetic route of green environmental protection, low cost, easy realization, few side reactions, high selectivity, high yield and high purity of azoxystrobin is of great significance

Method used

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  • Preparation method of kresoxim-methyl
  • Preparation method of kresoxim-methyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: 2-(2-methylphenoxymethyl)bromobenzene (Ⅲ 1 ) preparation

[0069] To a 1000 ml four-necked flask connected with stirring, a thermometer, a constant pressure dropping funnel and a reflux condenser, add 400 g of 1,2-dichloroethane, 82.8 g (0.6 mol) of potassium carbonate, 108.2 g (1.0 mol) ) 2-methylphenol, heated, kept between 40 and 45°C, added dropwise 215.8 grams (1.05 moles) of 2-chloromethylbromobenzene (Ⅱ 1 ), the dropwise addition was completed in about 3 hours, after which the reaction was stirred at 45 to 55°C for 2 hours, cooled to 20-25°C, filtered, the filter cake was washed with 1,2-dichloroethane, 100 grams each time, and the organic phases were combined, Distillation recovery solvent, underpressure distillation (145-165 ℃ / 1-2mmHg) obtains 259.2 grams of 2-(2-methylphenoxymethyl) bromobenzene (Ⅲ 1 ), yield 93.4%, gas phase purity 99.8%.

[0070] The NMR data of the resulting product are as follows:

[0071] 1 H NMR (400MHz, DMSO-d 6 ):δ:

...

Embodiment 2

[0073] Example 2: 2-(2-methylphenoxymethyl)bromobenzene (Ⅲ 1 ) preparation

[0074] In a 1000 ml four-neck flask connected with stirring, a thermometer, a constant pressure dropping funnel and a reflux condenser, add 500 g of dichloromethane, 82.8 g (0.6 mol) of potassium carbonate, 108.2 g (1.0 mol) of 2-methyl Phenol, heated, kept between 30 and 35°C, added dropwise 262.5 grams (1.05 moles) of 2-bromomethyl bromobenzene (Ⅱ 2 ), the dropwise addition was completed in about 3 hours, thereafter 35 to 40°C stirred and reacted for 2 hours, cooled to 20-25°C, filtered, the filter cake was washed with dichloromethane, 100 grams each time, the organic phases were combined, the solvent was recovered by distillation, and the Pressure distillation (145-165 ℃ / 1-2mmHg) obtains 257.6 grams of 2-(2,5-dimethylphenoxymethyl) bromobenzene (Ⅲ 1 ), yield 92.8%, gas phase purity 99.8%.

Embodiment 3

[0075] Embodiment 3: the preparation of 2-(2-methylphenoxymethyl) phenyl oxalate methyl ester (V)

[0076] Under nitrogen protection, 150 grams of tetrahydrofuran, 2.7 grams (0.11 moles) of magnesium powder, 0.5 grams of 1,2-dibromoethane, 1.5 grams of 2 prepared in Example 1 were added to a 500 milliliter four-necked flask equipped with a stirring and thermometer. -(2-methylphenoxymethyl)bromobenzene(Ⅲ 1 ), 0.05 gram of iodine, after triggering the Grignard reaction at 40-45°C for 0.2 hours, 26.2 grams (0.1 moles in total) of 2-(2-methylphenoxymethyl) prepared in Example 1 were added dropwise between 40-45°C ) Bromobenzene(Ⅲ 1 ) and 100 g of tetrahydrofuran, drop it in 2 hours, then stir and react at 45-50° C. for 3 hours to obtain a reaction solution containing Grignard reagent. Cool to 20-25°C, transfer the resulting reaction solution containing the Grignard reagent to a constant pressure dropping funnel, keep it between 20-25°C, and add it dropwise to a solution containi...

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Abstract

The invention provides a preparation method of kresoxim-methyl, which comprises the following steps: carrying out an etherification reaction on 2-halogenated methyl halogenated benzene and 2-methylphenol to prepare 2 -(2-methylphenoxy methyl) halogenated benzene, and carrying out a Grignard reaction on the 2-(2-methylphenoxy methyl) halogenated benzene and magnesium metal to prepare reaction liquid containing a Grignard reagent; dropwise adding the obtained reaction liquid containing the Grignard reagent into dimethyl oxalate to prepare 2-(2-methyl phenoxy methyl) phenyl methyl oxalate, and finally performing condensation reaction with methoxylamine salt to prepare kresoxim-methyl. The method has the advantages of cheap and accessible raw materials and low cost; the method has the advantages of short process flow, easy realization of reaction conditions, safe, simple and convenient operation, less process wastewater generation amount, greenness and environmental protection, and can prepare kresoxim-methyl only through three steps of reactions; raw materials and intermediate products are high in stability, high in reaction activity and selectivity and less in side reaction; and theobtained kresoxim-methyl has few impurities and high purity and yield, and is beneficial to industrial production of kresoxim-methyl.

Description

technical field [0001] The invention relates to a preparation method of kresoxim-methyl, which belongs to the technical field of pesticide chemistry. Background technique [0002] Kresoxim-methyl (I), the English name is Kresoxim-methyl, the CAS number is 143390-89-0, and the English chemical name is (E)-α-(methoxyimino)-2-((2-methylphenoxy)methyl)benzeneacetic acid methylester , its structural formula is as follows: [0003] [0004] Kresoxim-methyl was developed by BASF in 1992 and became one of the two varieties of Strobilurin fungicides that first entered the market in 1996. It is a new type of natural Strobilurin fungicide developed as a lead compound Agricultural fungicides have a unique mechanism of action, broad-spectrum and high-efficiency activity, and high selectivity. They are safe for crops, humans, animals, and beneficial organisms, and basically have no pollution to the environment. They are effective against strawberry powdery mildew, melon powdery mildew...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/04C07C251/48C07C41/16C07C43/205C07C67/343C07C69/738
CPCC07C249/04C07C41/16C07C67/343C07C43/205C07C69/738C07C251/48
Inventor 吕强三戚聿新王海涛
Owner XINFA PHARMA
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