Preparation method of alkyl borate

A technology of alkyl borate and diboronic acid pinacol ester, which is applied in the field of preparation of alkyl borate, can solve the problems of high catalyst cost and few convenient and universal methods, and achieve good functional group compatibility, Wide range of raw material sources and simple feeding methods

Inactive Publication Date: 2018-01-12
UNIV OF SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although there are many synthetic methods of alkyl borate esters, there are not many convenient and universal methods. Some reactions require the addition of ligands with complex structures, and some require the formation of complexes of corresponding metals and ligands as catalysts. Some catalysts have the disadvantage of high cost

Method used

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  • Preparation method of alkyl borate
  • Preparation method of alkyl borate
  • Preparation method of alkyl borate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The reaction formula of this embodiment is as follows:

[0042]

[0043] (1) Under air, silver pentafluoropropionate (10mol%) and lithium tert-butoxide (2eq) were added to a pressure-resistant sealed reaction tube containing magnetons. Under the protection of argon, add 1 mL of 1,4-dioxane to the reaction tube, stir at room temperature for 20 minutes, then add pinacol diboronate (1.25 eq) and 4-benzene Add butyl-2-p-toluenesulfonate (0.25mmol) into the reaction liquid, stopper the stopper, place in a 60°C oil bath and stir for 24 hours.

[0044](2) Cool the material obtained in step (1) to room temperature, add ethyl acetate and mix thoroughly, filter the solid residue with a short silica gel column, and keep the organic phase.

[0045] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a crude product, and then purify the crude product with a silica gel column. The eluent is a mixed solution of petroleum ether and ethyl acetate, and the r...

Embodiment 2～14

[0048] The compounds in Table 1 were prepared according to the method of Example 1.

[0049] Table 1 Example 1~14 product structure and characterization data

[0050]

[0051]

[0052]

Embodiment 15～20

[0054] The raw materials of Example 1 were used to replace the catalyst and alkali to prepare alkyl borates, and the yields are shown in Table 2.

[0055] Table 2 embodiment 15~20 catalyst, alkali and productive rate summary

[0056]

[0057]

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Abstract

The invention provides a preparation method of alkyl borate. The preparation method comprises the following step: reacting by taking alkyl tosylate and bisdiboron shown as a formula I-a as raw materials under the action of a silver catalyst and alkali to obtain the alkyl borate shown as the formula I. According to the preparation method provided by the invention, commercially-available silver saltis directly adopted for participating into the reaction, a reaction system and a feeding mode are simple, and no ligand needs to be added. The used bisdiboron is insensitive to air and water and further is more convenient in actual application. The alkyl tosylate as the raw material can be conveniently prepared from alkyl alcohol and the raw material is wide in source; meanwhile, first-stage or second-stage alkyl borate is obtained by silver catalysis direct carbon-oxygen bond fission of the alkyl tosylate and the bisdiboron; the reaction has good functional group compatibility.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing an alkyl borate. Background technique [0002] Organoboron chemistry has been developed from scratch and has always been an extremely important part of the field of chemistry. The discovery of the Suzuki coupling reaction allows organoboronic acid ester compounds to be effectively used in the construction of carbon-carbon bonds. It is not only widely sought after in the field of organic synthesis, but also widely used in the fields of materials chemistry and medicinal chemistry. . Therefore, efficient and convenient synthesis of organic borate raw materials is particularly important. At present, the representative preparation methods of organic borate compounds are as follows: [0003] (1) The synthetic method of traditional organic borate is to use Grignard reagent or lithium reagent to react with electrophilic boron compound (Organometallics ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 张奔傅尧张祯琦
Owner UNIV OF SCI & TECH OF CHINA
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