Method for high-purity and high-yield preparation of p-chlorophenylboronic acid

A high-yield technology of p-chlorophenylboronic acid, applied in the fields of medicinal chemistry and material chemistry, can solve the problems of large environmental pollution, low purity, and many solid wastes, and achieves reduced environmental pollution, high product purity, and good reaction effect. Effect

Inactive Publication Date: 2017-07-14
安徽至善新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem mainly solved by the present invention is to provide a method for preparing p-chlorophenylboronic acid with high purity and

Method used

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  • Method for high-purity and high-yield preparation of p-chlorophenylboronic acid
  • Method for high-purity and high-yield preparation of p-chlorophenylboronic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0023] A method for preparing p-chlorophenylboronic acid with high purity and high yield is provided, and the specific preparation process of said p-chlorophenylboronic acid is:

[0024] (1) Grignard reagent preparation:

[0025] Under the protection of nitrogen, add 666.46g of newly produced magnesium chips and 13L of butyl ether into the 50L reaction kettle, stir, and heat to 120°C. Add a small amount of p-chlorophenylmagnesium bromide butyl ether solution to the reaction system, and after stirring for 5 minutes, add dropwise a mixture of 3.84kg of 1,4-dichlorobenzene and 13L of n-butyl ether, trigger for 10min, and complete the dropwise addition after 2h. Maintain stirring for 8h, stop the reaction, and obtain the Grignard reagent.

[0026] (2) Preparation of p-chlorophenylboronic acid:

[0027] Under nitrogen protection, tributyl borate (7.21kg, 31.33mol) and 10L butyl ether were added to a 100L low-temperature reactor, and the temperature was lowered to -70°C under mech...

Embodiment 2

[0032] The difference between this embodiment and the specific implementation case 1 is that p-chlorobromobenzene was added dropwise in step (1), and 3.76 kg of the product was obtained, with a yield of 92.1% and an HPLC content of 99.5%. Other implementation manners are the same as the specific case 1.

Embodiment 3

[0034] The difference between this embodiment and specific implementation cases 1 to 2 is that the solvents used in the reaction of step (1) and step (2) are diethyl ether, ethylene glycol dimethyl ether, isopropyl ether, THF, and 2-methyltetrahydrofuran. Other implementation modes are the same as the specific implementation cases 1 to 2. The reaction results are shown in the table below.

[0035]

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PUM

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Abstract

The invention discloses a method for high-purity and high-yield preparation of p-chlorophenylboronic acid. The method comprises: (1) carrying out a Grignard reaction on magnesium chips and 1,4-dichlorobenzene under the action of an initiator to obtain a 4-chlorophenyl magnesium chloride Grignard reagent; and (2) carrying out a deep low temperature reaction on the 4-chlorophenyl magnesium chloride Grignard reagent obtained in the step (1) and trialkyl borate, carrying out acidolysis, and treating to obtain p-chlorophenylboronic acid. With the technical scheme of the present invention, the raw material cost and the production cost are substantially reduced, the reaction effect is good, the conversion rate during the boronization reaction is increased, the generation of the by-product impurities is reduced, the post-treatment is simple, the product purity is high, and the environmental pollution is reduced.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and material chemistry, in particular to a method for preparing p-chlorophenylboronic acid with high purity and high yield. Background technique [0002] Since arylboronic acid was first used as an organic intermediate in 1880, there have been more and more applications and researches on boric acid in various fields. Various preparation methods have been applied to the synthesis of substituted phenylboronic acid. There are three traditional preparation methods : (1) organolithium reagent method, (2) Grignard reagent method and (3) catalytic boronation method. The organolithium reagent method has a high yield and few by-products, but this method is dangerous in operation and the raw material is expensive, so it is not suitable for industrial production. The catalytic borylation method was derived after the discovery of the Suzuki coupling reaction, and it has good adaptability to various groups...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 魏开举陈重铭任明秀崔杨谢轶能
Owner 安徽至善新材料有限公司
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