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Method for synthesizing 2,3,4,5,6-pentafluorophenol

A technology of pentafluorophenol and pentafluorobromobenzene, which is applied in the field of compound preparation, can solve the problems of inconvenient operation, difficult preparation, and low yield, and achieve the effects of reducing the use of expensive reagents, facilitating industrial production, and reducing costs

Active Publication Date: 2014-05-14
SUZHOU HIGHFINE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, in JP2005082548, the target compound 2, 3, 4, 5, 6-pentafluorophenol is obtained by oxidation with pentafluorophenylboronic acid as the starting material, but the starting material is expensive and difficult to prepare, and the method is inconvenient to operate ; In CN102887817, the target compound 2, 3, 4, 5, 6-pentafluorophenol is obtained by using pentafluorohalogenated benzene as the starting material through hydrolysis and acidification, but high temperature, pressure and strong alkaline conditions are required, which is not conducive to industrial production; In the literature reported by Qing-Yun Chen et al., it involves the by-products in the paper research, and the preparation process involves formatting reactions, which is not conducive to industrial production
These reported synthetic methods have shortcomings such as low yield, high cost, and unfavorable industrial production, so they cannot meet the needs of the fields of medicine, pesticides, and liquid crystal materials.

Method used

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  • Method for synthesizing 2,3,4,5,6-pentafluorophenol
  • Method for synthesizing 2,3,4,5,6-pentafluorophenol

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Experimental program
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Effect test

Embodiment 1

[0024] Preparation of compound (II), namely benzyl-protected pentafluorophenol.

[0025] At room temperature, add 95 mg of cuprous iodide, 0.15 g of 8-hydroxyquinoline, 4.24 g of potassium phosphate, N 2 Under protection, add 1.25 ml of pentafluorobromobenzene and 10 ml of benzyl alcohol of the formula (I) with a syringe, slowly heat to 100°C, and react for 24 hours. After the reaction, cool down to room temperature. The reaction solution was diluted with dichloromethane, filtered, the filter cake was washed with dichloromethane, and the solvent was evaporated to obtain 2.2 g of compound (II), with a yield of 80%.

[0026] The NMR and mass spectrum data of compound (II) are as follows:

[0027]

Embodiment 2

[0029] Preparation of compound (II), namely benzyl-protected pentafluorophenol.

[0030] At room temperature, add 95 mg of cuprous iodide, 0.15 g of 8-hydroxyquinoline, 4.24 g of potassium phosphate, N 2 Under protection, add 1.25 ml of pentafluorobromobenzene of formula (I) and 10 ml of benzyl alcohol with a syringe, slowly heat to 110°C, and react for 36 hours. After the reaction, cool down to room temperature. The reaction solution was diluted with dichloromethane, filtered, the filter cake was washed with dichloromethane, and the solvent was evaporated to obtain 2.24 g of compound (II), with a yield of 82%.

[0031] The NMR and mass spectrum data of compound (II) are as follows:

[0032]

Embodiment 3

[0034] Preparation of compound (II), namely benzyl-protected pentafluorophenol.

[0035] At room temperature, add 95 mg of cuprous iodide, 0.15 g of 8-hydroxyquinoline, 4.24 g of potassium phosphate, N 2 Under protection, add 1.25 ml of pentafluorobromobenzene of formula (I) and 10 ml of benzyl alcohol with a syringe, heat slowly to 120°C, and react for 24 hours. After the reaction, cool down to room temperature. The reaction solution was diluted with dichloromethane, filtered, the filter cake was washed with dichloromethane, and the solvent was evaporated to obtain 2.16 g of compound (II), with a yield of 79%.

[0036] The NMR and mass spectrum data of compound (II) are as follows:

[0037]

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Abstract

The invention provides a method for synthesizing 2,3,4,5,6-pentafluorophenol. The method comprises the steps of (a) carrying out Ullmann reaction on bromopentafluorobenzene as shown in a formula (I) and benzyl alcohol in an inert gas atmosphere under the action of a catalyst cuprous iodide, a ligand and an inorganic base at 100-120 DEG C, and then generating a compound (II), and (b) reacting the compound (II) in an alcoholic solvent in the presence of hydrogen under the action of a palladium carbon catalyst at 20-50 DEG C, and removing the benzyl group, thereby obtaining a compound (III), namely, the 2,3,4,5,6-pentafluorophenol. The method is simple, low in cost and high in yield, and applicable to industrial production. The synthetic route of the method is as shown in specification.

Description

technical field [0001] The present invention relates to the technical field of compound preparation, in particular to a method for preparing intermediates of medicine or liquid crystal materials, and more particularly to a method for synthesizing 2, 3, 4, 5, 6-pentafluorophenol. Background technique [0002] Pentafluorophenol is an important medicine, pesticide and liquid crystal material intermediate, and because it can activate carboxyl groups and promote the formation of peptide bonds, it is also widely used in peptide synthesis. [0003] The synthetic documents of 2,3,4,5,6-pentafluorophenol reported at present have the documents published by JP2005082548, CN102887817 and Qing-Yun Chen etc. (J. Chem. Soc., Perkin Trans. 2,1991, 1071-1075 ). Among them, in JP2005082548, the target compound 2, 3, 4, 5, 6-pentafluorophenol is obtained by oxidation with pentafluorophenylboronic acid as the starting material, but the starting material is expensive and difficult to prepare, a...

Claims

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Application Information

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IPC IPC(8): C07C39/27C07C37/055
CPCC07C37/055C07C41/16C07C39/27C07C43/225
Inventor 蒋兆芹孙豪义陆雪根吕敏杰
Owner SUZHOU HIGHFINE BIOTECH
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