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Separation and purification method of 2-(4-fluorophenyl) thiophene

A purification method and fluorophenyl technology are applied in the field of separation and purification of 2-thiophene, and can solve the problems of long time consumption, difficulty in industrial production, and difficulty in separation and purification.

Active Publication Date: 2014-02-26
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is difficult to separate and purify
The traditional column chromatography separation method is cumbersome to operate, takes a long time, and is not conducive to industrial production
At present, in the domestic and foreign literature about synthesizing this compound, only mention utilizes column chromatography to separate this compound, but this method is loaded down with trivial details to operate, is difficult for industrialized production
At present, there is no special discussion on the separation and purification of this compound in the relevant literature at home and abroad.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] (1) Synthesis of 2-(4-fluorophenyl)thiophene:

[0016] in Ar 2 Under protection, add dissolved toluene: ethanol: Na to a 250mL round bottom flask 2 CO 3 0.139 g (1 mmol) of 4-fluorophenylboronic acid in a 2:1:1 mixed solution. Add 0.023g Pd(PPh 3 ) 4 , stirred for 5 minutes, added 0.163g of 2-bromothiophene, refluxed in an oil bath at 80°C, and stirred electromagnetically for 24h.

[0017] (2) Separation and purification of 2-(4-fluorophenyl)thiophene:

[0018] ① extract the organic phase of the reaction mixture with dichloromethane, and dry it with anhydrous sodium sulfate for subsequent use;

[0019] ②The mixture was filtered with suction and fractionated under reduced pressure at 90°C.

[0020] ③Heat petroleum ether to 60°C, add the remaining residue of step ② until it does not dissolve, then add a small amount of petroleum ether to dissolve most of the residue. Suction filtration, down to room temperature, to obtain the pure 2-(4-fluorophenyl)thiophene.

Embodiment 2

[0022] (1) Synthesis of 2-(4-fluorophenyl)thiophene:

[0023] in Ar 2 Under protection, add dissolved toluene: ethanol: Na to a 250mL round bottom flask 2 CO 3 0.139 g (1 mmol) of 4-fluorophenylboronic acid in a 2:1:1 mixed solution. Add 0.023g Pd(PPh 3 ) 4 , stirred for 5 minutes, added 0.163g of 2-bromothiophene, refluxed in an oil bath at 80°C, and stirred electromagnetically for 24h.

[0024] (2) Separation and purification of 2-(4-fluorophenyl)thiophene:

[0025] ① extract the organic phase of the reaction mixture with ethyl acetate, and dry it with anhydrous sodium sulfate for subsequent use;

[0026] ②The mixture was filtered with suction and fractionated under reduced pressure at 84°C.

[0027] ③Heat petroleum ether to 60°C, add the remaining residue of step ② until it does not dissolve, then add a small amount of petroleum ether to dissolve most of the residue. Suction filtration, down to room temperature, to obtain the pure 2-(4-fluorophenyl)thiophene.

Embodiment 3

[0029] (1) Synthesis of 2-(4-fluorophenyl)thiophene:

[0030] in Ar 2 Under protection, add dissolved toluene: ethanol: Na to a 250mL round bottom flask 2 CO 3 0.139 g (1 mmol) of 4-fluorophenylboronic acid as a 2:1:1 mixed solution. Add 0.023g Pd(PPh 3 ) 4 , stirred for 5 minutes, added 0.163g of 2-bromothiophene, refluxed in an oil bath at 80°C, and stirred electromagnetically for 24h.

[0031] (2) Separation and purification of 2-(4-fluorophenyl)thiophene:

[0032] ① extract the organic phase from the reaction mixture with chloroform, and dry it over anhydrous sodium sulfate for subsequent use;

[0033] ②The mixture was filtered with suction and fractionated under reduced pressure at 90°C.

[0034] ③Heat petroleum ether to 60°C, add the remaining residue of step ② until it does not dissolve, then add a small amount of petroleum ether to dissolve most of the residue. Suction filtration, down to room temperature, to obtain the pure 2-(4-fluorophenyl)thiophene.

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Abstract

The invention discloses a separation and purification method of 2-(4-fluorophenyl) thiophene and relates to a separation and purification method of a compound. The method comprises the steps: extracting a mixture obtained in a reaction by using an organic solvent A and drying anhydrous sodium sulfate for later use; carrying out suction filtration on mixed liquor and carrying out fractional distillation at a certain temperature B under reduced pressure; and heating petroleum ether to 60 DEG C, adding the rest residue till the residue is not dissolved, adding little petroleum ether to dissolve most residue, carrying out suction filtration, and cooling to room temperature, thus obtaining a pure substance of the 2-(4-fluorophenyl) thiophene. The 2-(4-fluorophenyl) thiophene is an important intermediate for synthetizing an anti-diabetic medicine Canagliflozin. The method for purifying the 2-(4-fluorophenyl) thiophene through a recrystallization method, which is disclosed by the invention, is simple and convenient in operation and high in yield and is very suitable for industrial production.

Description

technical field [0001] The invention relates to a method for separating and purifying compounds, in particular to a method for separating and purifying 2-(4-fluorophenyl)thiophene. Background technique [0002] Canagliflozin is one of the new anti-diabetic drugs with the best clinical effect in recent years. 2-(4-Fluorophenyl)thiophene is an important intermediate in the synthesis of this compound. 2-(4-fluorophenyl)thiophene is an important intermediate in the synthesis of antidiabetic drug Canagliflozin, so the crude product 2-(4-fluorophenyl)thiophene needs to be purified. The compound has special physical properties, it is a white solid at room temperature, and it is liquid under heating conditions. Therefore, it is difficult to separate and purify. The traditional column chromatography separation method is cumbersome to operate, takes a long time, and is not conducive to industrial production. At present, domestic and foreign literature on the synthesis of this ...

Claims

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Application Information

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IPC IPC(8): C07D333/12
CPCC07D333/12
Inventor 孟艳秋刘文虎丁一杨哲
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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