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Method for synthesizing 1,4-di(difluoro phenoxy methyl) benzene

A technology of difluorophenoxymethyl and synthetic method, which is applied in the field of 1, can solve the problems of unsuitability for industrialized production, high risk of sodium hydride, high price, etc., and achieve cheap raw materials, short reaction time, and convenient operation Effect

Inactive Publication Date: 2018-10-16
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] This type of unimolecular radical nucleophilic substitution reaction can be used to synthesize 1,4-bis(chlorodifluoromethyl)benzene, but the price of 1,4-bis(chlorodifluoromethyl)benzene with higher purity is more expensive , the sodium hydride used in the reaction is also dangerous and inconvenient to operate, so it is not suitable for industrial production

Method used

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  • Method for synthesizing 1,4-di(difluoro phenoxy methyl) benzene
  • Method for synthesizing 1,4-di(difluoro phenoxy methyl) benzene

Examples

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Embodiment 1

[0029] Add 5.0g of 1,4-bis(difluoromethyl)benzene, 50mL of carbon tetrachloride, and 0.25g of benzoyl peroxide into the three-neck flask, replace the air, blow in chlorine gas, and stir at 80°C for 9h. After the completion of the reaction monitored by thin-layer chromatography, nitrogen gas was blown in to replace the dissolved chlorine in the reaction solution. After the gas replacement was completed, the organic phase was washed with water until neutral. Use sodium thiosulfate solution to wash the organic phase to remove benzoyl peroxide until the starch potassium iodide test paper does not change color. The organic phase was separated and washed 3 times with water. The organic phase was dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 9.07 g of a crude 1,4-bis(chlorodifluoromethyl)benzene product as a colorless oil.

[0030] Under nitrogen atmosphere, 9.07g of...

Embodiment 2

[0032] Add 5.0 g of 1,4-bis(difluoromethyl)benzene, 50 mL of chloroform, and 1 g of lauryl peroxide into a three-neck flask, replace the air with chlorine gas, and stir at 80°C for 9 h. After the completion of the reaction monitored by thin-layer chromatography, nitrogen gas was blown in to replace the dissolved chlorine in the reaction solution. After the gas replacement was completed, the organic phase was washed with water until neutral. Use sodium thiosulfate solution to wash the organic phase to remove benzoyl peroxide until the starch potassium iodide test paper does not change color. The organic phase was separated and washed 3 times with water. The organic phase was dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 9.35 g of crude product of 1,4-bis(chlorodifluoromethyl)benzene as a colorless oil.

[0033] Under nitrogen atmosphere, 9.35g of the above crud...

Embodiment 3

[0035] Add 5.0g of 1,4-bis(difluoromethyl)benzene, 50mL of trichlorobenzene, and 0.5g of tert-butyl peroxyvaleric acid to a three-neck flask, replace the air with chlorine gas, and stir at 80°C for 9h . After the completion of the reaction monitored by thin-layer chromatography, nitrogen gas was blown in to replace the dissolved chlorine in the reaction solution. After the gas replacement was completed, the organic phase was washed with water until neutral. Use sodium thiosulfate solution to wash the organic phase to remove benzoyl peroxide until the starch potassium iodide test paper does not change color. The organic phase was separated and washed 3 times with water. The organic phase was dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 8.98 g of a crude 1,4-bis(chlorodifluoromethyl)benzene product as a colorless oil.

[0036]Under a nitrogen atmosphere, 8.98g...

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Abstract

The invention provides a method for synthesizing 1,4-di(difluoro phenoxy methyl) benzene. The method comprises the following steps: (1) by taking 1,4-di(difluoro methyl) benzene as an initial raw material, and carrying out a free radical substation reaction with chlorine in the presence of a free radical initiator so as to obtain 1,4-di(chlorine difluoro methyl) benzene; (2) without refining of the intermittent, namely the 1,4-di(chlorine difluoro methyl) benzene, directly carrying out a unimolecule free radical nucleophilic substitution reaction on the intermittent with an alkali and phenol in an organic solvent, and carrying out recrystallization on a crude product, thereby obtaining the 1,4-di(difluoro phenoxy methyl) benzene. The method is gentle in reaction condition, and the obtainedproduct is high in both yield and purity and is applicable to large-scale production.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a synthesis method of 1,4-bis(difluorophenoxymethyl)benzene. Background technique [0002] Parylene series film, also known as polyparaxylylene film, Chinese name Parylene, is a kind of advanced coating material in the world today. It is composed of p-xylene ring dimer and its derivatives through vacuum vapor deposition polymerization. It is widely used in aerospace, military weapons, biomedicine, micro-electronic mechanical systems due to its good chemical stability, biocompatibility, excellent mechanical, electrical, and thermal properties, and moisture-proof, mildew-proof, and salt-proof properties. and cultural relics protection and many other fields. Parylene HT film is the latest commercialized product in the Parylene series of films, and it is the most advanced type of coating material in the world today. In addition to the good chemical stability, biocompatibil...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/225C07C17/14C07C22/08
CPCC07C17/14C07C41/16C07C43/225C07C22/08
Inventor 肖国民王华政潘东辉宋相海张佳慧缪亚男杨红美徐宁宁朱艳丽
Owner SOUTHEAST UNIV
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