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Preparation method of improved 2-(2'-bromomethylphenyl)-2-carbonyl methyl acetate

A kind of technology of methyl carbonyl acetate and bromomethyl phenyl, applied in the field of preparation of 2-(2'-bromomethyl phenyl-2-methyl carbonyl acetate, it can solve the problem of rising cost, polluting the environment and wasting energy and other problems, to achieve the effect of improving the reaction method and improving the yield

Inactive Publication Date: 2013-12-18
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But also there are some deficiencies in industrialization: 2-methylbenzoyl chloride is easily hydrolyzed into acid in the reaction process, thereby resulting in a reduction in the yield of 2-methylbenzoyl nitrile; the bromination process needs light irradiation to waste energy, The use of toxic solvents (such as carbon tetrachloride) pollutes the environment, the use of catalysts increases the cost, and the generation of more by-products during the reaction makes it difficult to separate and purify the target compound, etc.

Method used

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  • Preparation method of improved 2-(2'-bromomethylphenyl)-2-carbonyl methyl acetate
  • Preparation method of improved 2-(2'-bromomethylphenyl)-2-carbonyl methyl acetate
  • Preparation method of improved 2-(2'-bromomethylphenyl)-2-carbonyl methyl acetate

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Effect test

Embodiment 1

[0021] In a 500ml round bottom flask, add A27.9g (180mmol), sodium cyanide 9.3g (190mmol), tetrabutylammonium bromide 1.5g (4.6mmol), tin dichloride 0.11g (0.6mmol), iodine 0.15g (0.6mmol) and toluene 200ml. The system was heated up to 70° C., and reacted at this temperature for 4 hours, and the conversion rate of the raw material was about 65% according to gas chromatography of the reaction liquid. At this time, the system was lowered to room temperature (20° C.), and 50 ml of aqueous sodium hydroxide solution with pH=10 was added to the reaction bottle, and the stirring reaction was continued for 1 hour. TLC detected that the reaction was complete. The system was neutralized with 5% aqueous sodium bicarbonate solution, filtered, separated, the aqueous phase was extracted twice with 50 ml of toluene, and the organic phases were combined and dried. 24.2 g of the crude product was obtained by precipitation, the content was 79.3%, and the yield was 73%.

Embodiment 2

[0023] In a 500ml round bottom flask, add A27.9g (180mmol), sodium cyanide 9.3g (190mmol), tetrabutylammonium bromide 1.5g (4.6mmol), tin dichloride 0.11g (0.6mmol), iodine 0.15g (0.6mmol) and toluene 200ml. The system was heated up to 80° C., and reacted at this temperature for 4 hours, and the conversion rate of the raw material was about 75% according to gas chromatography of the reaction liquid. At this time, the system was lowered to room temperature (20° C.), and 50 ml of aqueous sodium hydroxide solution with pH=10 was added to the reaction bottle, and the stirring reaction was continued for 1 hour. TLC detected that the reaction was complete. The system was neutralized with 5% aqueous sodium bicarbonate solution, filtered, separated, the aqueous phase was extracted twice with 50 ml of toluene, and the organic phases were combined and dried. 23.7 g of the crude product was obtained by precipitation, the content was 88.7%, and the yield was 80%.

Embodiment 3

[0025] A27.9g (180mmol), sodium cyanide 9.3g (190mmol), tetrabutylammonium bromide 1.5g (4.6mmol) and toluene 200ml were added in a 500ml round bottom flask. The system was heated up to 80° C., and reacted at this temperature for 4 hours, and the conversion rate of the raw material was about 45% according to gas chromatography of the reaction liquid. At this time, the system was lowered to room temperature (20° C.), and 50 ml of aqueous sodium hydroxide solution with pH=10 was added to the reaction flask, and the stirring reaction was continued for 1 hour. TLC detected that the reaction was complete. The system was neutralized with 5% aqueous sodium bicarbonate solution, filtered, separated, the aqueous phase was extracted twice with 50 ml of toluene, and the organic phases were combined and dried. 22.9 g of the crude product was obtained by precipitation, the content was 60%, and the yield was 52%.

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Abstract

The invention relates to a process synthesis method of an improved trifloxystrobin intermediate 2-(2'-bromomethylphenyl)-2-carbonyl methyl acetate. The innovation of the process is reflected in the following two reaction steps: (1) 2-methyl benzoyl chloride reacts with cyanide to generate 2-methyl benzoyl cyanide, and (2) 2-(2'-methylphenyl)-2-carbonyl methyl acetate is brominated to generate 2-(2'- bromomethylphenyl)-2-carbonyl methyl acetate. The method provided by the invention is used for solving the following problems that the hydrolysis of the 2-methyl benzoyl chloride causes low synthesis yield of the 2-methyl benzoyl cyanide, light is needed in the bromination process to waste energy source, a solvent with large toxicity is used, the numerous generated dibromides are difficult to separate and purify, the yield is low and the like in the previous synthesis. According to the method provided by the invention, the operation is simpler and the reaction conditions are milder. Especially, the yield is greatly increased and the production cost is reduced, so that the method is suitable for industrial production.

Description

Technical field [0001] The invention relates to a preparation method of 2-(2'-bromomethylphenyl-2-carbonylacetic acid methyl ester) technical background [0002] Methoxyacrylate compounds are a type of fungicides successfully developed based on the natural product Strobilurins. As a respiratory inhibitor of fungi, it has a unique mechanism of action. It can be strongly adsorbed by the plant wax layer, providing excellent protection for the plant surface. The characteristic of this type of fungicide compound is that it has a carbon-carbon double bond or a carbon-nitrogen double bond in its pharmacophore part. Methyl 2-(2'-bromomethylphenyl)-2-carbonylacetate is the synthetic pharmacophore part. It is the key intermediate of this type of compounds with carbon-nitrogen double bonds, such as trifloxystrobin and tristrostrobin. There are many routes in the synthesis of the intermediate 2-(2’-bromomethylphenyl)-2-carbonyl acetate methyl ester being studied at home and abroad, bu...

Claims

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Application Information

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IPC IPC(8): C07C69/738C07C67/313C07C251/48C07C249/12
Inventor 徐凤波胡方中姜文涛祝冠斌王文虎李庆山
Owner NANKAI UNIV
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