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 , the effect of high yield

Active Publication Date: 2020-11-03
YANTAI DERUN LIQUID CRYSTAL MATERIALS
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  • Application Information

AI Technical Summary

Benefits of technology

This new method uses certain chemical compounds called benzene or naphthalenediols (B) instead of existing methods that require expensive starting material like pimellicum bifunctionaleanone). By adding B's hydroxy group at position 4 on their structure, they form an intermediate product between two different molecules containing one type of phenoxyane moiety. These intermediates then react together under specific conditions to create various types of substances known collectively as azo dyes.

Problems solved by technology

Technologies described involve different methods for producing specific types of aryllidodimensional arenas called napthenols from natural sources like plants. These include synthetic routes involving expensive starting materials and complicated processes due to instabilities during storage. To overcome these issues, new techniques including transitional metal catalysations, photoinitiated chemistry, and copper catalysis were developed.

Method used

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preparation example Construction

[0032] The invention provides a preparation method of aryl borate, which is characterized in that it comprises the following steps: in the presence of a water-soluble free radical initiator, water is used as a solvent, and arylsulfonyl chloride and biboronic acid pinacol ester are used as The raw materials are reacted to obtain aryl borate.

[0033] According to the preparation method of an aryl borate according to 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 described in 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 aryl borate ester described in the present invention, further preferably, the water-soluble azo radical initiator is selected from 2,2'-azo

Embodiment 1

[0043]Add 100ml of water, 0.1mol of benzenesulfonyl chloride, 0.1mol of biboronic acid pinacol ester into the reaction bottle, stir well, then add 0.01mol of 2,2'-azobis(2-methylpropylamidine) disalt salt, slowly raise the temperature to 50°C, keep the reaction at this temperature for 10h, the whole reaction process is in a stirring state, after the reaction, slowly cool the system to room temperature, extract 3 times with ethyl acetate, collect the organic phase , 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 of water, 0.1mol of benzenesulfonyl chloride, 0.2mol of biboronic acid pinacol ester to the reaction flask, stir well, then add 0.01mol of 2,2'-azobis[2-(2-imidazoline-2- Base) propane] dihydrochloride, slowly raise the temperature to 100°C, keep the temperature for 5h, the whole reaction process is in a stirring state, after the reaction, slowly cool the system to room temperature, use dichloromethane to extract The organic phase was collected three times, distilled under reduced pressure, and dried in vacuo to obtain a white solid phenylboronic acid pinacol ester with a yield of 93.5% and a purity of 95.1%.

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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, reacting by using water as a solventand aryl sulfonyl chloride and bis(pinacolato)borate as raw materials, extracting the reaction product by using an organic solvent after the reaction is completed, collecting the extract an organic phase, and carrying out reduced pressure distillation to obtain the product aryl borate. By using the water-soluble free radical initiator, water can be used as a reaction solvent; compared with the prior art that acetonitrile, halogenated alkane, ethyl acetate and other organic solvents are used, water is used as a solvent, environmental pollution is reduced, toxicity is reduced, and raw material sources are more economical; in addition, the method has the advantages of mild reaction, simple post-treatment, high yield, high purity and the like, and is very suitable for industrial production.

Description

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Claims

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Application Information

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Owner YANTAI DERUN LIQUID CRYSTAL MATERIALS
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