Method and apparatus for continuously producing aryl boric acid

An aryl boronic acid and aryl technology, which is applied in the field of continuous preparation of organic boronic acids, can solve the problems of difficulty in improving reaction yield and production efficiency, and achieve the effects of shortening residence time, continuous production and improving reaction yield.

Inactive Publication Date: 2011-09-21
BAYER TECH & ENG SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can also achieve a relatively continuous reaction, it is still difficult to improve the reaction yield and production efficiency.

Method used

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  • Method and apparatus for continuously producing aryl boric acid
  • Method and apparatus for continuously producing aryl boric acid
  • Method and apparatus for continuously producing aryl boric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of 3-thiophene boronic acid

[0037] Pass the 3-bromothiophene / tetrahydrofuran solution with a flow rate of 9mL / min and a molar concentration of 0.75mol / L and a butyllithium / n-hexane solution with a flow rate of 3mL / min and a molar concentration of 2.7mol / L through the heat exchanger. 242 and 244 are pre-cooled to -50°C and injected into the first micromixer 10 to mix. Subsequently, it is mixed with the n-butyl borate / tetrahydrofuran solution with a flow rate of 9 mL / min and a molar concentration of 0.9 mol / L, which is pre-cooled to -50°C by the heat exchanger 246, through the second micro mixer 220, and then enters the micro reactor The reaction was carried out at 230, and the reaction temperature was controlled to -45°C. The residence volume of the mixture of 3-bromothiophene and butyllithium is 530 μL, including the inside of the first micromixer 210, the outlet of the first micromixer 210 and the inlet of the second micromixer 220, and the residence time is ...

Embodiment 2

[0043] Synthesis of 5-pyrimidine boronic acid

[0044] Pass the 5-bromopyrimidine / tetrahydrofuran solution with a flow rate of 27mL / min and a molar concentration of 0.25mol / L and a butyllithium / n-hexane solution with a flow rate of 6mL / min and a molar concentration of 2.7mol / L through the heat exchanger. 242 and 244 are pre-cooled to -65°C and injected into the first micromixer 210 to mix. Subsequently, it is mixed with the n-butyl borate / tetrahydrofuran solution with a flow rate of 11 mL / min and a molar concentration of 0.6 mol / L, which is precooled to -55°C by the heat exchanger 246, through the second micromixer 220, and then enters the microreactor The reaction was carried out at 230, and the reaction temperature was controlled to -50°C. The residence volume of the mixture of 5-bromopyrimidine and butyllithium is 440 μL, including the inside of the first micromixer 210, the outlet of the first micromixer 210 and the inlet of the second micromixer 220, and the residence time ...

Embodiment 3

[0047] Synthesis of 4-cyanophenylboronic acid

[0048] The 4-bromobenzonitrile / tetrahydrofuran solution with a flow rate of 11 mL / min and a molar concentration of 0.5 mol / L and a butyl lithium / n-hexane solution with a flow rate of 3 mL / min and a molar concentration of 2.2 mol / L were passed through heat exchange. The reactors 242 and 244 are pre-cooled to -65° C., and injected into the first micro mixer 210 for mixing. Subsequently, it is mixed with the n-butyl borate / tetrahydrofuran solution with a flow rate of 11 mL / min and a molar concentration of 0.6 mol / L, which is precooled to -55°C by the heat exchanger 246, through the second micromixer 220, and then enters the microreactor The reaction was carried out at 230, and the reaction temperature was controlled to -50°C. The residence volume of the mixture of 4-bromobenzonitrile and butyllithium is 440 μL, including the inside of the first micromixer 210, the outlet of the first micromixer 210, and the inlet of the second micromi...

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Abstract

The invention relates to a method and an apparatus for continuously producing aryl boric acid. The method comprises the following steps: a first mixture is obtained by mixing aryl halide or an aryl heterocyclic compound with lithium alkyl in a first micro mixer, and a stay period of the first mixture is 0.5 to 3 s; a second mixture is obtained by mixing the first mixture with boric acid ester in a second micro mixer; and aryl boric acid is prepared by carrying out a reaction on the second mixture in a micro reactor. According to the method and the apparatus provided by the invention, aryl boric acid can be prepared continuously, rapidly and safely to achieve industrialization of aryl boric acid.

Description

Technical field [0001] The invention relates to a method and device for continuously preparing organic boric acid, in particular to a method and device for continuously preparing arylboronic acid. Background technique [0002] As an important intermediate in the field of organic chemistry, organoboric acid compounds are widely used in Suzuki coupling reactions, glycol protection, biomedicine and other fields. Aryl boronic acid compounds are a type of organic boronic acid compounds. They are widely used in the formation of carbon-carbon bonds and carbon-heterobonds, such as carbon-oxygen bonds, carbon-nitrogen bonds and carbon-sulfur bonds. The downstream products are concentrated in medicine, Pesticides, liquid crystal materials and other fields. [0003] Aryl boronic acid compounds can be prepared by one-step or two-step organolithium reagent method. US7087755B1 discloses a method for preparing pyridine boronic acid, which is a one-step method for preparing aryl boronic acid. I...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 刘涛赵东波何华平
Owner BAYER TECH & ENG SHANGHAI
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