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Method for synthesizing 2-(4-fluorophenyl) thiophene

A technology of fluorophenyl and fluorophenylmagnesium bromide, which is applied in organic chemistry and other fields, and can solve problems such as high energy consumption, difficult purification, and low yield

Active Publication Date: 2016-07-13
HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the existing preparation method of 2-(4-fluorophenyl)thiophene, there are defects such as difficult acquisition of reaction raw materials, harsh reaction conditions, high energy consumption, high cost, low yield, and difficult purification.

Method used

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  • Method for synthesizing 2-(4-fluorophenyl) thiophene
  • Method for synthesizing 2-(4-fluorophenyl) thiophene
  • Method for synthesizing 2-(4-fluorophenyl) thiophene

Examples

Experimental program
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Effect test

Embodiment 1

[0042] (1) Each module (comprising pre-insulation module, first reaction module, second reaction module and quenching module) in the microchannel reactor system that material flows through is replaced with nitrogen;

[0043] (2) Dilute 4-fluorophenylmagnesium bromide with 2-methyltetrahydrofuran to a molar concentration of 0.3mol / L as material 1; dilute trimethyl borate to 0.5mol / L with 2-methyltetrahydrofuran Homogeneous mixed solution, as material 2; Material 1 and material 2 are respectively passed into such as figure 1 The shown first pre-insulation module 11 and the second pre-insulation module 12 are pre-insulated so that both are at -5°C;

[0044] (3) After material 1 and material 2 are pre-insulated, they are all passed into the first reaction module, such as figure 1 As shown, material 1 and material 2 are mixed and reacted in the first reaction module 21, then continue to react in two second reaction modules 22, the reaction temperature in the first reaction module ...

Embodiment 2

[0050] (1) Each module (comprising pre-insulation module, first reaction module, second reaction module and quenching module) in the microchannel reactor system that material flows through is replaced with nitrogen;

[0051] (2) Dilute 4-fluorophenylmagnesium bromide with tetrahydrofuran to a molar concentration of 0.4mol / L as material 1; dilute trimethyl borate with tetrahydrofuran to a homogeneous mixed solution of 0.5mol / L as material 2; Pass material 1 and material 2 respectively into such as figure 1 The shown first pre-insulation module 11 and the second pre-insulation module 12 are pre-insulated so that they are both at 0°C;

[0052] (3) After material 1 and material 2 are pre-insulated, they are all passed into the first reaction module, such as figure 1 As shown, material 1 and material 2 are mixed and reacted in the first reaction module 21, and then continue to react in two second reaction modules 22, and the reaction temperature in the first reaction module and th...

Embodiment 3

[0058] (1) Each module (comprising pre-insulation module, first reaction module, second reaction module and quenching module) in the microchannel reactor system that material flows through is replaced with nitrogen;

[0059] (2) Dilute 4-fluorophenylmagnesium bromide with tetrahydrofuran to a concentration of 0.3mol / L as material 1; dilute trimethyl borate with tetrahydrofuran into a homogeneous mixed solution of 0.4mol / L as material 2; Pass material 1 and material 2 respectively into such as figure 1 The shown first pre-insulation module 11 and the second pre-insulation module 12 are pre-insulated so that both are at -5°C;

[0060] (3) After material 1 and material 2 are pre-insulated, they are all passed into the first reaction module, such as figure 1As shown, material 1 and material 2 are mixed and reacted in the first reaction module 21, then continue to react in two second reaction modules 22, the reaction temperature in the first reaction module and the two second reac...

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Abstract

The invention discloses a method for synthesizing 2-(4-fluorophenyl) thiophene. The method comprises the following steps: 1) preparing 4-fluorophenylboronic acid: separately preserving heat for a 4-fluorophenylmagnesium bromide solution which is taken as a material 1 and a boric acid ester solution which is taken as a material 2 to the reaction temperature, carrying out mixing reaction, and carrying quenching and post-treatment to obtain 4-fluorophenylboronic acid; and 2) preparing 2-(4-fluorophenyl) thiophene): adding the 4-fluorophenylboronic acid, 2-bromo thiophene and a Pd catalyst into an organic solvent to dissolve to obtain a material 3, separately preserving the heat for the material 3 and an inorganic alkali aqueous solution which is taken as a material 4 to the reaction temperature, carrying out mixing reaction, and carrying out post-treatment to obtain 2-(4-fluorophenyl) thiophene. The method is simple in operation process, is short in production period, is gentle in condition, is fewer in side reactions and is high in yield; and the obtained product is high in purity.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a method for synthesizing 2-(4-fluorophenyl)thiophene. Background technique [0002] Canagliflozin is a drug for treating diabetes, and its clinical performance in treating type Ⅱ diabetes is outstanding. Its structural formula is as follows: [0003] [0004] Among them, 2-(4-fluorophenyl)thiophene is an important intermediate for the synthesis of canagliflozin. 2-(4-fluorophenyl)thiophene, molecular formula C 10 h 7 FS, with a molecular weight of 178.23, is an off-white powdery solid at room temperature, and its structural formula is as follows: [0005] [0006] In the existing preparation method of 2-(4-fluorophenyl)thiophene, there are defects such as difficult to obtain reaction raw materials, harsh reaction conditions, high energy consumption, high cost, low yield and difficult purification. In order to overcome the shortcomings and deficiencies of the above-mention...

Claims

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Application Information

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IPC IPC(8): C07D333/12
CPCC07D333/12
Inventor 杨昆安永生
Owner HEILONGJIANG XINCHUANG BIOLOGICAL TECH DEV CO LTD
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