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Preparation method of methyl 4-bromoacetyl-2-methylbenzoate

A technology for methyl methyl benzoate and methyl benzoic acid, applied in the field of preparation of methyl 4-bromoacetyl-2-methyl benzoate, meeting the requirements of simple equipment and experimental conditions, mild reaction conditions, and low raw material cost cheap effect

Active Publication Date: 2019-04-02
荆门医药工业技术研究院 +1
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  • Claims
  • Application Information

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Problems solved by technology

[0008] At present, there is no relevant literature report, so the preparation of 4-bromoacetyl-2-methylbenzoic acid methyl ester seems more important

Method used

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  • Preparation method of methyl 4-bromoacetyl-2-methylbenzoate
  • Preparation method of methyl 4-bromoacetyl-2-methylbenzoate

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Embodiment Construction

[0025] Preferred examples of the invention will be described in detail below. The examples given are to better understand the content of the invention, and the content of the invention is not limited to the examples. Non-essential improvements and adjustments to the embodiment according to the content of the invention still belong to the scope of the invention.

[0026] Synthesis of the first intermediate compound

[0027] In a 500ml one-necked flask, add 4-bromo-2-methylbenzoic acid (20g, 9.3mmol), add methanol 160g, add concentrated sulfuric acid 2ml, heat and reflux for 6 hours, TLC detects that the reaction is complete, add hydrated ethyl acetate, Extracted twice, dried over anhydrous sodium sulfate, and spin-dried to obtain the first intermediate compound (methyl 4-bromo-2-methylbenzoate) as a white solid.

[0028] Synthesis of the second intermediate compound

[0029] In a 500ml single-necked flask, add methyl 4-bromo-2-methylbenzoate (15g, 6.6mmol), 90g of tetrahydro...

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Abstract

The invention provides a preparation method of methyl 4-bromoacetyl-2-methylbenzoate. The preparation method comprises the following steps: (1) dissolving 4-bromo-2-methylbenzoic acid in methanol, andperforming an esterification reaction under the catalytic action of sulfuric acid so as to produce a first intermediate compound; (2) performing a reaction between the first intermediate compound with potassium vinyl fluoroborate or vinyl boronic acid under the catalytic action of palladium so as to obtain a second intermediate compound; and (3) performing an alpha-halogenated ketone synthesis reaction on the second intermediate compound under the action of a halogenating reagent so as to obtain the methyl 4-bromoacetyl-2-methylbenzoate. The preparation method has the advantages of low raw material cost, a short route, mild reaction conditions, simple requirements for equipment and experimental conditions, large-scale amplification synthesis and a high application value.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of methyl 4-bromoacetyl-2-methylbenzoate. Background technique [0002] Fluralaner, the chemical name is 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-trifluoromethyl-3-isoxazolyl]-2-methyl-nitrogen- [2-Oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl]-benzamide, its structural formula is: [0003] [0004] Fluralaner, a new ectoparasiticide belonging to the isoxazolone class, is a systemic drug that kills fleas and lice. The product can be used to control flea bite atopic dermatitis and was launched in Germany, Spain, Italy, France, the Netherlands and the UK in April 2014. [0005] At present, there are few documents on the synthesis of Fluralaner. One of the feasible methods is to use 4-bromoacetyl-2-methylbenzoic acid methyl ester to close the ring with 3,5-dichlorotrifluoroacetylbenzene, and then combine with 2- Amino-N-(2,2,2-trifluoroethyl)acetamide is condens...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/78C07C67/08C07C67/343C07C67/313
CPCC07C67/08C07C67/313C07C67/343C07C69/78
Inventor 许方亮赵琳李立威
Owner 荆门医药工业技术研究院
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