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A kind of synthetic method of 4-fluoro-2,3-dimethylphenyl methanesulfonate

A technology of dimethylphenyl mesylate and dimethylphenyl ether, which is applied in the field of organic synthesis, can solve the problems of expensive palladium-carbon noble metal catalysts, increased preparation costs, and high environmental protection pressure, so as to reduce the difficulty of synthesis, The effect of reducing preparation cost and reducing environmental pressure

Active Publication Date: 2022-03-22
西安淳甄新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method uses 4-nitro 2,3-dimethylphenol as the starting material to directly react with methanesulfonate, and the process route is simple and clear, but the disadvantage is that the palladium-carbon noble metal catalyst used is relatively expensive, which increases the preparation cost , and the last step of diazotization reaction produces a large amount of waste water, and the pressure on environmental protection is high

Method used

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  • A kind of synthetic method of 4-fluoro-2,3-dimethylphenyl methanesulfonate
  • A kind of synthetic method of 4-fluoro-2,3-dimethylphenyl methanesulfonate
  • A kind of synthetic method of 4-fluoro-2,3-dimethylphenyl methanesulfonate

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Embodiment 1

[0028] This embodiment includes the following steps:

[0029] Step 1. Add 120g of acetic acid into a 500mL three-necked flask, then turn on the stirring device for stirring, add 30g of 3-fluoroxylene and 0.3g of iodic acid in turn, and then control the temperature in the three-necked flask to -5~5℃. 42g of bromine was added dropwise, and after the dropwise addition was completed, the reaction was maintained at -5 to 5°C for 8 hours to obtain a reaction solution containing 4-fluoro-2,3-dimethylbromobenzene; the solution containing 4-fluoro-2,3 -The reaction solution of dimethylbromobenzene is added to 2400g of water, and then 210g of DCM (methylene chloride) is added for extraction, and an equal amount of DCM is added to extract three times in total, and the organic phases separated after the three extractions are combined, Then add the sodium bicarbonate solution that 10g sodium bicarbonate is prepared with 1000g water, 1000g water wash successively, the organic phase that obt...

Embodiment 2

[0039] This embodiment includes the following steps:

[0040] Step 1. Add 240g of acetic acid into a 1000mL three-necked flask, then turn on the stirring device for stirring, add 60g of 3-fluoroxylene and 0.6g of iodic acid in turn, and then control the temperature in the three-necked flask to -5~5℃. 84g of bromine was added dropwise, and after the dropwise addition was completed, the reaction was maintained at -5 to 5°C for 8 hours to obtain a reaction solution containing 4-fluoro-2,3-dimethylbromobenzene; -The reaction solution of dimethylbromobenzene is added to 4800g water and then added 420g of DCM (dichloromethane) for extraction, each time an equal amount of DCM is added for a total of three extractions, the organic phases separated after three extractions are combined, Then add the sodium bicarbonate solution that 10g sodium bicarbonate is prepared with 1000g water, 1000g water wash successively, the organic phase that obtains is dried and filtered with 100g anhydrous ...

Embodiment 3

[0047] This embodiment includes the following steps:

[0048] Step 1. Add 240g of acetic acid into a 1000mL three-necked flask, then turn on the stirring device for stirring, add 60g of 3-fluoroxylene and 0.6g of iodic acid in turn, and then control the temperature in the three-necked flask to -5~5℃. 84g of bromine was added dropwise, and after the dropwise addition was completed, the reaction was maintained at -5 to 5°C for 8 hours to obtain a reaction solution containing 4-fluoro-2,3-dimethylbromobenzene; -The reaction solution of dimethylbromobenzene is added to 4800g water and then added 420g of DCM (dichloromethane) for extraction, each time an equal amount of DCM is added for a total of three extractions, the organic phases separated after three extractions are combined, Then add the sodium bicarbonate solution that 10g sodium bicarbonate is prepared with 1000g water, 1000g water wash successively, the organic phase that obtains is dried and filtered with 100g anhydrous ...

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Abstract

The invention discloses a method for synthesizing 4-fluoro-2,3-dimethylphenyl methanesulfonate. The method comprises: 1. 3-fluoro-xylene undergoes halogenation reaction to obtain 4-fluoro-2,3 ‑Dimethylhalobenzene; two, 4‑fluoro‑2,3‑dimethylhalogenated benzenes are coupled to obtain 4‑fluoro‑2,3‑dimethylphenyl ether; three, 4‑fluoro‑ Hydrolysis of 2,3-dimethylphenyl ether gives 4-fluoro-2,3-dimethylphenol; four, 4-fluoro-2,3-dimethylphenol and methylsulfonyl chloride undergo esterification to obtain 4 ‑Fluoro‑2,3‑dimethylphenyl mesylate. The present invention uses 3-fluoroxylene as a raw material, undergoes halogenation, coupling, hydrolysis and esterification reactions sequentially, and through combined design of different types of reactions, improves the 4-fluoro-2,3-dimethylphenyl The yield of mesylate can be improved while avoiding the use of expensive catalysts or raw materials, which reduces the preparation cost, reduces waste water discharge, and reduces the pressure on environmental protection.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of 4-fluoro-2,3-dimethylphenyl methanesulfonate. Background technique [0002] 4-Fluoro-2,3-dimethylphenyl methanesulfonate is a new type of chemical, which can be used as an intermediate for pesticides, medicines, liquid crystals and organic electroluminescent materials, and has a large potential market demand. Publication No. CN108602765 patent discloses the preparation method of 4-fluoro-2,3-dimethylphenyl methanesulfonate: first, 4-nitro-2,3-dimethylphenol is prepared under the condition of triethylamine React with methanesulfonyl chloride to generate 4-nitro-2,3-dimethylsulfonate, and then hydrogenate the nitro group through palladium carbon to obtain 4-amino-2,3-dimethylphenylmethanesulfonate , and then use sodium nitrite in pyridine hydrogen fluoride solution for diazotization to obtain the target product. The method uses...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/28C07C309/66
CPCC07C303/28C07C37/055C07C41/16C07C17/12C07C309/66C07C39/27C07C43/225C07C25/13
Inventor 梁腾吴阳方勇闫路
Owner 西安淳甄新材料有限公司
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