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A kind of preparation method of pentafluorophenol

A technology of pentafluorophenol and compounds, applied in the field of preparation of pentafluorophenol, which can solve the problems of increased production cost, expensive production cost, and expensive raw material cost

Active Publication Date: 2020-08-25
SHANGHAI CHEMSPEC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] 1. Using hexafluorobenzene as raw material, the cost of raw material is expensive, and there are many by-products
[0019] 2. Using pentafluorobromobenzene as raw material, high temperature and high pressure is not conducive to large-scale production, and the production cost is expensive
[0020] 3. Using pentafluorobromobenzene to synthesize pentafluorophenylboronic acid, and then oxidizing it to obtain pentafluorophenol, although the cost of raw materials is low, the process route is long, and expensive Grignard reagents are needed, which increases the production cost

Method used

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  • A kind of preparation method of pentafluorophenol
  • A kind of preparation method of pentafluorophenol
  • A kind of preparation method of pentafluorophenol

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preparation example Construction

[0065] The present invention provides a kind of preparation method of pentafluorophenol, the structure of described pentafluorophenol is as shown in formula I:

[0066]

[0067] The preparation method of pentafluorophenol provided by the present invention may comprise Hoffman rearrangement reaction, and described Hoffman rearrangement reaction specifically comprises: under the condition that the compound of formula II is carried out Hoffman rearrangement under the condition that alkali, halogenating reagent exist Exhaust reaction, preparation obtains formula III compound, and reaction equation is as follows:

[0068]

[0069] In the preparation method of pentafluorophenol provided by the present invention, the Hofmann rearrangement reaction can be carried out in a reaction solvent, and those skilled in the art can make the reaction according to the reaction raw materials (for example, formula II compound, alkali, halogenating reagent, etc.) Select the appropriate solvent...

Embodiment 1

[0086] Add 68g of sodium hydroxide to 1200g of water at 0-10°C. Add 75g of bromine dropwise to aqueous sodium hydroxide solution, and stir at 0-10°C for 1h. 90g of pentafluorobenzamide solid was added in batches to the above reaction solution, and the internal temperature was controlled to 80°C for reaction. After the reaction was completed, the temperature was lowered to 20°C, 200g of methyl tert-butyl ether was added to the reaction solution, stirred, left standing, and separated into layers, and the organic phase was concentrated at 30°C to obtain 69g of pentafluoroaniline with a yield of 89.5%, which was analyzed by HPLC , content >95%.

Embodiment 2-6

[0088] The kind of organic solvent is changed, and other is with embodiment 1, and its result is shown in Table 1:

[0089] Table 1

[0090]

[0091]

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Abstract

The invention relates to the field of organic synthesis and especially relates to a preparation method for pentafluorophenol. The preparation method comprises the steps of: 1) a Hoffmann rearrangement reaction: performing the rearrangement reaction to the compound (II) in the presence of alkali and a halogenation reagent to prepare the compound (III); 2) a diazo-hydrolysis reaction: performing a diazotization reaction to the compound (III) with a nitroso compound and performing a hydrolysis reaction in the presence of a catalyst to prepare the compound (I). The raw materials in the method are easy to obtain. The preparation method is short in synthesis route and is mild in reaction conditions, is simple in purification of the product, has high product purity and stable product quality, is low in cost of the whole synthesis route and is suitable for industrial large-scale promotion and application.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of pentafluorophenol. Background technique [0002] Pentafluorophenol is an important chemical intermediate widely used in the fields of medicine and electronic materials. [0003] Pentafluorophenol is mostly used to prepare pentafluorophenyl active esters for peptide synthesis, thereby promoting the formation of peptide bonds. Alkyl esters that activate the carboxyl group as an amino acid protecting group, the rate of reaction to form a peptide bond is very slow. Phenyl esters have higher reactivity. If there is a strong electronegative substituent on the benzene ring, the rate of aminolysis will be similar to that of acid anhydride. Because one of the most important requirements for peptide bond formation is high reaction efficiency and no side reactions, pentafluorophenol esters have been widely used in peptide synthesis. Pentafluorophenol esters can b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/045C07C39/27
CPCC07C37/045C07C209/56C07C245/20C07C39/27C07C211/52
Inventor 许智汪奇辉崔永涛李桂云赵子强孙中岳
Owner SHANGHAI CHEMSPEC CORP
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