Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of aryl borate

A technology of aryl borate and diboronic acid pinacol ester, which is applied in the field of synthesis of aryl borate, can solve the problems of low yield and unsuitability for industrial production, and achieve reduced toxicity and economical source of raw materials , mild effect

Active Publication Date: 2022-07-15
YANTAI DERUN LIQUID CRYSTAL MATERIALS
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Using aryl sulfonyl chloride and biboronic acid pinacol ester as raw materials, free radical coupling reaction occurs under the action of ultraviolet light and dipotassium hydrogen phosphate to generate aryl borate. Acyl chloride is a raw material, and it can be carried out at room temperature, but the yield is not very high, and it is also not suitable for industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0032] The invention provides a preparation method of aryl borate, which is characterized by comprising the following steps: in the presence of a water-soluble free radical initiator, using water as a solvent, using aryl sulfonyl chloride and biboronic acid pinacol ester as a solvent The raw materials are reacted to obtain an aryl boronate ester.

[0033] According to the preparation method of an aromatic boronate ester of the present invention, further preferably, the arylsulfonyl chloride is phenylsulfonyl chloride, p-tolylsulfonyl chloride, o-tolylsulfonyl chloride or m-tolylsulfonyl chloride acid chloride.

[0034] According to the preparation method of an aryl borate ester of the present invention, the water-soluble free radical initiator is a water-soluble azo free radical initiator.

[0035] According to the preparation method of an aromatic boronate ester of the present invention, further preferably, the water-soluble azo radical initiator is selected from 2,2'-azobis...

Embodiment 1

[0043]Add 100ml of water, 0.1mol of benzenesulfonyl chloride, 0.1mol of biboronic acid pinacol ester to the reaction flask, stir well, and then add 0.01mol of 2,2'-azobis(2-methylpropylamidine) disalt acid salt, slowly raise the temperature to 50 °C, and keep the reaction at this temperature for 10 h. The whole reaction process is in a state of stirring. After the reaction is completed, the system is slowly cooled to room temperature, extracted with ethyl acetate for 3 times, and the organic phase is collected. , distilled under reduced pressure, and dried in vacuo to obtain a white solid phenylboronic acid pinacol ester with a yield of 88.1% and a purity of 95.6%.

Embodiment 2

[0045] Add 100ml water, 0.1mol benzenesulfonyl chloride, 0.2mol biboronic acid pinacol ester to the reaction flask, stir well, then add 0.01mol 2,2'-azobis[2-(2-imidazoline-2- base) propane] dihydrochloride, slowly increase the temperature to 100 ° C, keep the temperature for 5 h, the whole reaction process is in a stirring state, after the reaction is completed, the system is slowly cooled to room temperature, extracted with dichloromethane Three times, the organic phase was collected, distilled under reduced pressure, and vacuum dried to obtain a white solid phenylboronic acid pinacol ester with a yield of 93.5% and a purity of 95.1%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation method of aryl borate, which mainly comprises the following steps: in the presence of a water-soluble free radical initiator, using water as a solvent, using aryl sulfonyl chloride and biboronic acid pinacol ester as raw materials to react , after the reaction is completed, use organic solvent extraction, collect the organic phase, and distill under reduced pressure to obtain the product aryl borate. The present invention uses a water-soluble free radical initiator, and can use water as a reaction solvent. Compared with the use of organic solvents such as acetonitrile, halogenated alkane, and ethyl acetate in the prior art, using water as a solvent not only reduces environmental pollution, but also reduces toxicity. , and the source of raw materials is more economical. In addition, the invention also has the advantages of mild reaction, simple post-processing, high yield and high purity, and is very suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing aryl boronate esters. Background technique [0002] Aromatic boronic esters are boronic ester compounds with single benzene ring or polycyclic aromatic hydrocarbons. Various substituted aryl boronic esters are important organic synthesis intermediates and intermediates of pharmaceuticals and pesticides. They are used in the preparation of biologically active reagents or materials. Research also has a wide range of applications. Substituted aryl boronic esters are important organic intermediates and molecular building blocks, which can participate in a wide variety of organic chemical reactions to construct more complex target compounds, such as Suzuki cross-coupling reaction, asymmetric synthesis of amino acids, Amino compound catalysts, etc. In biology, medicine or materials science, aryl borates have been used as sensors for hydrocarbons,...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 李娟袁晓丹
Owner YANTAI DERUN LIQUID CRYSTAL MATERIALS