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Method for preparing tert-butoxycarbonyl phenylboronic acid

A technology of tert-butoxycarbonylphenylboronic acid and carboxyphenylboronic acid, which is applied in the field of preparation of tert-butoxycarbonylphenylboronic acid, can solve the problem that the reaction time is as long as 24 hours, and achieves the convenience of large-scale industrial production, stable process conditions, Simple operation effect

Inactive Publication Date: 2015-11-04
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the literature description, the reaction needs to be operated at -78°C, and the reaction equipment is a sealed tank, which is dangerous, and the reaction time is as long as 24 hours

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] 10L glass reactor equipped with mechanical stirring, thermometer and constant pressure dropping funnel, add 3 moles of raw materials o-carboxyphenylboronic acid and 4 kg of tetrahydrofuran under nitrogen protection, add 3.3 moles of thionyl chloride dropwise under reflux stirring, react for 4 hours, cool down to 0 -5°C, add 4.8 moles of sodium tert-butoxide in batches, continue stirring for 1 hour after adding, add 2 kg of water, acidify with acetic acid, let stand, and separate the liquids. The organic phase was concentrated to obtain a crude product, which was recrystallized by adding 2 kg of petroleum ether to obtain a solid product o-tert-butoxycarbonylphenylboronic acid with a purity of 96% and a molar yield of 82%.

Embodiment 2

[0021] 10L glass reactor equipped with mechanical stirring, thermometer and constant pressure dropping funnel, add 3 moles of raw materials o-carboxyphenylboronic acid and 4 kg of tetrahydrofuran under nitrogen protection, add 3.3 moles of thionyl chloride dropwise under reflux stirring, react for 4 hours, cool down to 0 -5°C, add 5 moles of potassium tert-butoxide in batches, continue to stir and react for 1 hour after adding, add 2 kg of water, acidify with acetic acid, stand still, and separate the liquids. The organic phase was concentrated to obtain a crude product, which was recrystallized by adding 2 kg of petroleum ether to obtain a solid product o-tert-butoxycarbonylphenylboronic acid with a purity of 98% and a molar yield of 88%.

Embodiment 3

[0023] 10L glass reactor equipped with mechanical stirring, thermometer and constant pressure dropping funnel, add 3 moles of raw material m-carboxyphenylboronic acid and 4 kg of tetrahydrofuran under nitrogen protection, add 4.5 moles of thionyl chloride dropwise under reflux stirring, react for 4 hours, cool down to 0 -5°C, add 7.5 moles of potassium tert-butoxide in batches, continue to stir and react for 1 hour after adding, add 2 kg of water, acidify with acetic acid, let stand, and separate the liquids. The organic phase was concentrated to obtain a crude product, which was recrystallized by adding 2 kg of petroleum ether to obtain a solid product m-tert-butoxycarbonylphenylboronic acid with a purity of 98% and a molar yield of 95%.

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PUM

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Abstract

The present invention discloses a method for preparing tert-butoxycarbonyl phenylboronic acid, and relates to the field of organic synthesis, and the tert-butoxycarbonyl phenylboronic acid is prepared from carbonyl phenylboronic acid as a raw material by one-pot method in the effect of thionyl chloride and tert-butyl alcohol base. The inexpensive and readily available raw material is used, the cost of production is dramatically reduced, the method is suitable for preparation of o-tert-butoxycarbonyl phenylboronic acid, m-tert-butoxycarbonyl phenylboronic acid, and p-tert-butoxycarbonyl phenylboronic acid; and highest product molar yield is 95%, purity reaches 98%, process conditions are stable, operation is easy, and industrial mass production is easy to achieve.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing tert-butoxycarbonylphenylboronic acid. Background technique: [0002] Tert-butoxycarbonylphenylboronic acid compounds include o-tert-butoxycarbonylphenylboronic acid, m-tert-butoxycarbonylphenylboronic acid and p-tert-butoxycarbonylphenylboronic acid. It is an important intermediate for the synthesis of antitumor drugs. At this stage, the methods for preparing tert-butoxycarbonylphenylboronic acid compounds mainly include the following types: [0003] 1. Literature [Chemical Communications, Vol.48, 2012, p 11211-11213], using tert-butyl o-bromobenzoate as raw material, in tetrahydrofuran, under low temperature conditions, using sec-butyllithium and borate reaction process to Preparation of o-tert-butoxycarbonylphenylboronate. Although o-tert-butoxycarbonylphenylboronic acid ester can be further hydrolyzed into o-tert-butoxycarbonylphenylboronic...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 杨青张浩赵士民徐剑霄汪洪湖
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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