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4-amino-3-fluorophenol and preparation method thereof

A technology of p-aminophenol and fluorophenol, which is applied in the field of 4-amino-3-fluorophenol and its preparation, can solve the problems of high price, high cost, and cumbersome post-treatment process, and achieve simple steps, low production cost, and post-processing Effects with simple processing steps

Inactive Publication Date: 2016-06-08
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this production process, fluorophenol is a relatively expensive production raw material, and its post-treatment process is cumbersome, and the cost of industrial production is relatively high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A preparation method of 4-amino-3-fluorophenol, comprising the following steps:

[0026] (1) Add p-nitrophenol to the mixed solution of water and ethanol, under the pressure of 0.2Mpa, control the temperature and maintain it at 70°C, under the catalysis of nickel metal catalyst, pass in hydrogen gas, catalytic hydrogenation, the reaction is completed Finally, filter to remove rare metals, cool and crystallize to obtain p-aminophenol;

[0027] (2) Carry out sulfonation reaction of p-aminophenol in concentrated sulfuric acid, control the temperature at 20°C to obtain 4-aminophenol-2-sulfonic acid substituted by hydroxyl group, under the catalysis of hydrogen fluoride, add xenon difluoride for reaction , and then reflux in dilute sulfuric acid to remove the sulfonic acid group, extract with an extractant, and adjust the temperature to 40°C and the pH value to 7.0 to extract 4-amino-3-fluorophenol.

[0028] The result shows that the yield is: 63%

Embodiment 2

[0030] A preparation method of 4-amino-3-fluorophenol, comprising the following steps:

[0031] (1) Add p-nitrophenol to the mixed solution of water and ethanol, under the pressure of 0.2Mpa, control the temperature and maintain it at 70°C, under the catalysis of nickel metal catalyst, pass in hydrogen gas, catalytic hydrogenation, the reaction is completed Finally, filter to remove rare metals, cool and crystallize to obtain p-aminophenol;

[0032] (2) Carry out sulfonation reaction of p-aminophenol in concentrated sulfuric acid, control the temperature at 25°C to obtain 4-aminophenol-2-sulfonic acid substituted by hydroxyl group, under the catalysis of hydrogen fluoride, add xenon difluoride for reaction , and then reflux in dilute sulfuric acid to remove the sulfonic acid group, extract with an extractant, and adjust the temperature to 32°C and the pH value to 6.5 to extract 4-amino-3-fluorophenol.

[0033] The result shows that the yield is: 58%

Embodiment 3

[0035] A preparation method of 4-amino-3-fluorophenol, comprising the following steps:

[0036] (1) Add p-nitrophenol to the mixed solution of water and ethanol, under the pressure of 0.4Mpa, control the temperature and maintain it at 85°C, under the catalysis of nickel metal catalyst, pass in hydrogen gas, catalytic hydrogenation, the reaction is completed Finally, filter to remove rare metals, cool and crystallize to obtain p-aminophenol;

[0037] (2) Carry out sulfonation reaction of p-aminophenol in concentrated sulfuric acid, control the temperature at 12°C to obtain 4-aminophenol-2-sulfonic acid substituted by hydroxyl group, under the catalysis of hydrogen fluoride, add xenon difluoride for reaction , and then reflux in dilute sulfuric acid to remove the sulfonic acid group, extract with an extractant, and adjust the temperature to 50°C and the pH value to 10.5 to extract 4-amino-3-fluorophenol.

[0038] The result shows that the yield is: 60%

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PUM

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Abstract

The invention discloses a 4-amino-3-fluorophenol and a preparation method thereof. 4-nitrophenol is taken as a raw material and has a sulfonation reaction firstly after catalytic hydrogenation, then a product has a fluoro-substitution reaction, fluorine has substitution at the 3 site, then a desulfonation reaction is performed, and a target product is obtained through extraction. According to the preparation method, 4-nitrophenol with lower cost is used as the raw material, so that the cost of the production raw material is reduced, aftertreatment steps are simple, and the method is suitable for large-scale industrial production.

Description

Technical field: [0001] The invention relates to the technical field of biomedicine, in particular to 4-amino-3-fluorophenol and a preparation method thereof. Background technique: [0002] 4-Amino-3-fluorophenol is a widely used raw material for pharmaceutical and pesticide active substances. Intermediates of hair dyes, etc. The fluorine substituent in the 4-amino-3-fluorophenol molecule greatly increases the lipophilicity of the entire molecule, thereby increasing the membrane permeability of the molecule, making it suitable as an active component intermediate of some drugs. [0003] U.S. Patent No. 5,545,754 discloses a preparation method for synthesizing 4-amino-3-fluorophenol with o-fluoronitrobenzene as a raw material. The raw material is in an aqueous solution of an acidic organic solvent, pressurized by hydrogen, and catalyzed by a catalyst to produce 4- Amino-3-fluorophenol. In this production process, fluorophenol is a relatively expensive production raw materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/76C07C213/08
CPCC07C213/02C07C213/08C07C303/06C07C303/22C07C215/76C07C309/49
Inventor 叶芳
Owner 叶芳
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