Preparation method of pentafluorophenol

A technology of pentafluorophenol and pentafluorobenzonitrile, which is applied in the field of preparation of pentafluorophenol, and can solve the problems of low safety, cumbersome operation steps, high cost of raw materials and processes, etc.

Active Publication Date: 2018-05-18
QUZHOU CHEMSPEC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above method has the disadvantages of cumbersome operation steps, high raw material and process costs, low safety, etc., which are not conducive to large-scale industrial production. Therefore, in order to meet the growing market demand, there is an urgent need for a production method with low manufacturing cost and short operating process in this field. Pentafluorophenol method

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  • Preparation method of pentafluorophenol
  • Preparation method of pentafluorophenol

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preparation example Construction

[0039] The present invention provides a kind of preparation method of pentafluorophenol (compound of formula VII), described preparation method can comprise: pentafluorobenzonitrile (compound of formula II) and bromoacetate (compound of formula I) in the condition that zinc powder exists Carry out the coupling reaction under acidic conditions, then hydrolyze and decarboxylate under acidic conditions to prepare pentafluoroacetophenone (compound of formula V), and the reaction equation is as follows:

[0040] coupling reaction:

[0041]

[0042] In the preparation method provided by the present invention, the coupling reaction can be carried out in the presence of a solvent, and those skilled in the art can select the appropriate type and amount of solvent so that the substance can be fully dispersed in the reaction system. The solvent can be an organic solvent, more specifically an ether solvent, and the ether solvent can be, for example, diethyl ether, methyl tert-butyl eth...

Embodiment 1

[0067] Add 10g of zinc powder and 60g of tetrahydrofuran into the reaction flask, add 19.3g of pentafluorobenzonitrile, add dropwise 3 drops of methanesulfonic acid, heat to reflux under nitrogen protection, slowly add 25g of ethyl bromoacetate dropwise, and reflux for 3 hours. Cool down to 20°C, add 80g of 20% hydrochloric acid dropwise, heat up to 70°C for hydrolysis and decarboxylation, and stir for 5 hours to complete the reaction. The temperature was raised for steam distillation, the fractions at 90-110°C were collected, and then the fractions were distilled at atmospheric pressure, and 15.6g of yellow liquid was collected at 130-135°C, which was pentafluoroacetophenone with a GC content of 99.5%.

[0068] In a water bath at room temperature, add 6 g of tap water to the reaction bottle, start stirring, slowly add 12 g of 98% concentrated sulfuric acid, slowly add 60 g of formic acid, the internal temperature is about 30 ° C, and add 15.6 g of raw material pentafluoroaceto...

Embodiment 2

[0072] Add 40g of zinc powder and 200g of tetrahydrofuran into the reaction flask, add 58g of pentafluorobenzonitrile, add dropwise 1ml of methanesulfonic acid, heat to reflux under nitrogen protection, slowly add dropwise 90g of methyl bromoacetate, and reflux for 3 hours. The temperature was lowered to 20° C., 100 g of 30% hydrochloric acid was added dropwise, and the organic layer was separated after reacting for 1 hour. 100 g of 30% hydrochloric acid was slowly added to the organic layer, and then the temperature was slowly raised to 70° C. for decarboxylation reaction, and the reaction was completed after stirring for 5 hours. The organic solvent was distilled off by raising the temperature, followed by steam distillation to obtain 51.3 g of a yellow liquid, namely pentafluoroacetophenone, with a GC content of >99%.

[0073] Put 50g of pentafluoroacetophenone and 250g of formic acid into the reaction kettle, turn on mechanical stirring and heat to 55-60°C, start to slowly...

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Abstract

The invention relates to the field of organic synthesis, in particular to a preparation method of pentafluorophenol. The preparation method of pentafluorophenol comprises the steps as follows: 1) pentafluorobenzonitrile and bromoacetic ester are subjected to a coupling reaction in the presence of zinc powder, hydrolysis and decarboxylation are performed under the acid condition, and pentafluoroacetophenone is prepared; 2) pentafluoroacetophenone is subjected to a Baeyer-Villiger reaction in the presence of an oxidizing agent, and pentafluorophenol is prepared after hydrolysis. The preparationmethod of pentafluorophenol comprises simple and short operation steps and is low in production cost, high in industrial operability and suitable for large-scale industrial production.

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 organic chemical intermediate commonly used in the fields of medicine, pesticides, and liquid crystal materials. Pentafluorophenol can be used to prepare pentafluorophenyl active esters for peptide synthesis, thereby promoting the formation of peptide bonds, so it has important development and application value and huge market demand. [0003] The common method for preparing pentafluorophenol is to use pentafluorobromobenzene as a raw material, undergo Grignard reaction and borate ester action to obtain pentafluorobenzeneboronic acid compounds, and then undergo oxidation and hydrolysis of hydrogen peroxide to obtain pentafluorophenol (JP2004082548); or Pentafluorobromobenzene reacts under high temperature and high pressure under copper salt and alkaline conditions, and generates pent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/27C07C37/055C07C67/42C07C69/157C07C45/67C07C49/807C07C67/313C07C69/738C07C249/02C07C251/24
CPCC07C37/0555C07C45/676C07C67/313C07C67/42C07C249/02C07C251/24C07C69/738C07C49/807C07C69/157C07C39/27
Inventor 袁云龙何立赵姗姗
Owner QUZHOU CHEMSPEC CORP
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