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Synthesis method of 1-phenylvinyl borate

A technology of phenyl vinyl borate and synthesis method, which is applied in the field of synthesis of phenyl vinyl borate, can solve the problem of high price, increased cost, and difficulty in obtaining 1-phenyl vinyl trifluoromethanesulfonate problems such as good reaction selectivity, reduced reagent cost, and easy post-processing

Active Publication Date: 2021-03-30
南通药明康德医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material 1-phenylvinyl trifluoromethanesulfonate used in this route is not easy to obtain and needs to be prepared. Potassium phenate is also used, which is also a relatively expensive reagent, which increases the cost of the process. Post-treatment requires column chromatography separation , not suitable for pilot scale-up
Also reported (1-bromovinyl) benzene and biboronic acid ester as raw material in this document, identical catalyst and reaction condition, obtain final product through column chromatography, although raw material (1-bromovinyl) benzene is cheap and easy to get , but the reagents used and the final post-treatment are not suitable for scale-up process production

Method used

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  • Synthesis method of 1-phenylvinyl borate
  • Synthesis method of 1-phenylvinyl borate
  • Synthesis method of 1-phenylvinyl borate

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Sodium phenoxide PhONa (95.13g ,0.82mol), KBr (97.52g, 0.82mol), triphenylphosphine PPh 3 (4.31g, 16.44mmol) and dichlorobis(triphenylphosphine)palladium Pd(PPh 3 ) 2 Cl 2 (7.68 g, 10.96 mmol). Stir for 16 hours at 70°C under the protection of inert gas. TLC (petroleum ether:ethyl acetate=15:1) showed that starting material 1 ((1-bromovinyl)benzene) was consumed and new compounds were formed. After the reaction mixture was filtered, the filtrate was concentrated under reduced pressure to remove the solvent. The concentrated solution was diluted with water and extracted with ethyl acetate solvent, the extracted organic layer was washed with brine, Na 2 SO 4 Dry, filter and concentrate under reduced pressure to obtain a crude product. The crude product was then diluted with petroleum ether and ethyl acetate, stirred for several hours, filtered, and the filtrate was collected and concentrated to obtain a solid, which was recrystallized at 0°C with petroleum ether t...

Embodiment 1

[0023] The reaction formula of embodiment 1 is as follows:

[0024]

Embodiment 2

[0026] See Example 1 for details of the reaction conditions. After the reaction mixture was filtered, the filtrate was concentrated under reduced pressure to remove the solvent. The concentrated solution was diluted with water and extracted with ethyl acetate solvent, the extracted organic layer was washed with brine, Na 2 SO 4 Dry, filter and concentrate under reduced pressure to obtain a crude product. The crude product was then diluted with petroleum ether and ethyl acetate, stirred for several hours, filtered, and the filtrate was collected and concentrated to obtain a solid, which was recrystallized at -10°C with petroleum ether: ethyl acetate = 10:1 to obtain the final product as a yellow solid (66.92g, 0.291mol, 53.2% yield).

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Abstract

The invention discloses a synthetic method of 1-phenylvinyl borate The preparation method comprises the following steps: by taking (1-bromovinyl)benzene 1 and diborate 2 as raw materials and sodium phenolate and potassium bromide as reaction reagents, heating the raw materials in methylbenzene to finish reaction, extracting, washing and concentrating the reaction solution to obtain a crude product, and performing pulping, low-temperature recrystallization and other operations which are easy for pilot scale-up to obtain the final product 1-phenylvinyl borate. The method replaces the raw material potassium phenate in the prior art, and the reagent cost is reduced. The invention solves the problems that in an existing route, raw materials are not easy to obtain, boric acid ester substituted products at different positions are easily generated, post-treatment needs column separation and the like and are not suitable for pilot scale-up. The invention provides a synthesis process which has the advantages of economical and easily available raw materials, good reaction selectivity and economical and easily operated post-treatment.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a synthesis method of phenyl vinyl borate. Background technique [0002] 1-Phenyl vinyl borate is an important intermediate in organic synthesis, which can be used to synthesize natural products, bioactive molecules and functional organic compounds. Currently, there is no process route available for pilot scale-up. [0003] There are few reports on the existing synthesis methods of 1-phenylvinyl borate. The literature (Journal of Organometallic Chemistry, 2001, vol.625, #1, p.47-53) reported the synthesis method of this compound, using phenylacetylene and biboronate as raw materials, using cuprous chloride as the main catalyst, Potassium acetate is used as a cocatalyst, and two borate ester products (formula II) containing two different positions of substitutions are synthesized in DMF, but there are difficulties in subsequent separation and purification. Similar r...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 周义亮张泽堂王帅王小平张治柳
Owner 南通药明康德医药科技有限公司
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