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A kind of coupling synthesis method of 4,4,4-trifluorobutanol

A technology of trifluorobutanol and cross-coupling reaction, applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxy compounds, etc., can solve the problems of low yield of synthetic routes, unfavorable industrialization and application, etc.

Active Publication Date: 2021-09-21
湖南有色郴州氟化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, the yields of currently used synthetic routes are relatively low, which is not conducive to the promotion and application of industrialization

Method used

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  • A kind of coupling synthesis method of 4,4,4-trifluorobutanol
  • A kind of coupling synthesis method of 4,4,4-trifluorobutanol
  • A kind of coupling synthesis method of 4,4,4-trifluorobutanol

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preparation example Construction

[0026] The invention provides a kind of preparation method of 4,4,4-trifluorobutanol, comprising the following steps:

[0027] In the presence of a catalyst, mixing 2,2,2-trifluoro-1-haloethane and 1-chloroethanol in a solvent to perform a cross-coupling reaction to obtain 4,4,4-trifluorobutanol;

[0028] The catalyst is a copper salt and an organic ligand;

[0029] The copper salt is cuprous halide and / or cupric chloride; the organic ligand is 2,2'-bipyridine, tetramethylethylenediamine and 4,4-di-tert-butyl-2,2,- One or more of bipyridines.

[0030] In the present invention, the catalyst is preferably added to the reaction device now, and nitrogen gas is introduced, and then 2,2,2-trifluoro-1-haloethane, 1-chloroethanol and solvent are added to react to obtain 4,4,4 - Trifluorobutanol.

[0031] In the present invention, the catalyst is a copper salt and an organic ligand, and the organic ligand can complex the copper salt in the catalyst to promote the catalytic reaction....

Embodiment 1

[0045]Add CuI (0.5mmol) and 2,2'-bipyridine (1.0mmol) into a 5mL Schlenk tube, pump nitrogen three times, and add 2mL THF, 2,2,2-trifluoro-1- Chloroethane (10mmol) and 1-chloroethanol (5mmol), after adding the materials, stopper the plug, and heat in an oil bath at 50°C for 8h. After the reaction, the solid was removed by filtration, and then the filtrate was washed with saturated brine, and the organic phase and the water phase were separated with a separatory funnel. The organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and the combined filtrate was vacuum rotary evaporated. The product was separated by column chromatography with a yield of 80%.

[0046] The proton and fluorine spectra of the product in this example are as follows Figure 1~2 shown by figure 1 with figure 2 It can be seen that the product prepared in this example is 4,4,4-trifluorobutanol.

Embodiment 2

[0048] Use CuCl instead of CuI to conduct experiments, add CuCl (0.5mmol) and 2,2'-bipyridine (1.0mmol) to a 5mL Schlenk tube, pump nitrogen three times, and add 2mL THF, 2,2, 2-Trifluoro-1-chloroethane (10mmol) and 1-chloroethanol (5mmol) were added, plugged with a stopper, and heated in an oil bath at 50°C for 8h. After the reaction, the solid was removed by filtration, and then the filtrate was washed with saturated brine, and the organic phase and the aqueous phase were separated with a separatory funnel. The organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, and the combined filtrate was vacuum rotary evaporated, and the column The product was isolated by chromatography in a yield of 61%.

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Abstract

The invention provides a novel method for coupling and synthesizing 4,4,4-trifluorobutanol, comprising the following steps: in the presence of a catalyst, 2,2,2-trifluoro-1-chloroethane and 1-chloroethanol is mixed in a solvent to carry out cross-coupling reaction to obtain 4,4,4-trifluorobutanol; the catalyst is a copper salt and an organic ligand; the copper salt is cuprous halide and / or chlorine copper chloride; the organic ligand is one or more of 2,2'-bipyridine, tetramethylethylenediamine and 4,4-di-tert-butyl-2,2,-bipyridine. The present invention uses copper salts and organic ligands as catalysts to catalyze the free radical cross-coupling reaction between 2,2,2-trifluoro-1 haloethane and 1-chloroethanol, and can efficiently prepare 4,4,4- Trifluorobutanol, the preparation method in the present invention has high selectivity and high yield. Experimental results show that the yield of the preparation method in the present invention is as high as 80%.

Description

technical field [0001] The invention belongs to the technical field of organic fluorine fine chemicals, and in particular relates to a novel coupling synthesis method for synthesizing 4,4,4-trifluorobutanol. Background technique [0002] 4,4,4-Trifluorobutanol is a widely used fluorine fine chemical. It is mainly used as a pharmaceutical raw material. It can be used to make antiseptics, antiemetics, and local analgesics. 10% ointment can be disinfected and sterilized, used as antiseptic, anesthetic, cosmetic preservative, and also an important raw material for many organic synthesis reactions. The following are the main operational routes of the synthetic trifluorobutanol reported in the literature at present: [0003] The method for preparing trifluorobutanol is to use 1,1,1-trifluoropropane and ethyl orthoformate as raw materials, reflux reaction in ether solution for a long time to generate fluorinated aldehyde, and then reduce it with lithium aluminum sodium hydride to ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C31/38C07C29/32
CPCC07C29/32C07C31/38
Inventor 王刚刘斌彭智敏李军李志鹏苏万里石芙蓉张振华
Owner 湖南有色郴州氟化学有限公司
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