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Method for preparing fluorine-containing substituted phenyl ketone

A technology of phenyl ketone and fluorobromobenzene, which is applied in the field of preparation of halogenated phenyl ketones, can solve the problems of lengthy and complex operation, instability, and harsh reaction temperature control, and achieve simple process, high conversion rate and mild conditions Effect

Active Publication Date: 2014-01-01
ASYMCHEM LAB TIANJIN +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction conditions of this method are relatively mild, the price of raw materials is relatively cheap, and the yield is high, but the operation is tedious and complicated. In the reaction, an unstable raw material such as acetaldehyde oxime is used, and the reaction temperature is controlled relatively harshly, which has a great impact on the yield. Not conducive to large-scale production

Method used

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  • Method for preparing fluorine-containing substituted phenyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of preparation 3,5-difluoroacetophenone The method is characterized in that the specific preparation steps are as follows:

[0026] (1) Add 712kg (5vol) of THF and 28kg (1.4eq) of magnesium powder into a 2000L reactor, and dropwise add 445kg of tetrahydrofuran (2vol) solution containing 160kg of the main raw material 3,5-difluorobromobenzene to prepare the Grignard reagent 3,5-Difluorophenylmagnesium bromide;

[0027] (2) Add 427kg (3vol) of tetrahydrofuran, 5.7kg (0.07eq) of cuprous chloride, 7.7kg (0.07eq) of aluminum trichloride, and 169.3kg (2.0eq) of acetic anhydride to another 3000L reactor in sequence. Add the above-mentioned Grignard reagent 3,5-difluorophenylmagnesium bromide dropwise at 10±2°C, and react at this temperature for 4 hours after dropping;

[0028] (3) After the reaction is complete, extract, wash the organic phase with brine, and concentrate to obtain the product 3,5-difluoroacetophenone 106kg, yield 82.0%, gas chromatography purity (G...

Embodiment 2

[0031] A kind of preparation o-fluoropropiophenone The method is characterized in that the specific preparation steps are as follows:

[0032] (1) Add 51.6kg (3vol) of 2-methyltetrahydrofuran (2-methyltetrahydrofuran) and 3.3kg (1.2eq) of magnesium powder to a 200L reactor, and dropwise add 17.2kg (1vol) of 2-methyltetrahydrofuran (2-methyltetrahydrofuran) containing 20kg of o-fluorobromobenzene as the main raw material Solution 37.2kg, prepared Grignard reagent o-fluorophenylmagnesium bromide;

[0033] (2) Add 34.4kg (2vol) of 2-methyltetrahydrofuran, 0.9kg (0.05eq) of ferric chloride, 0.8kg (0.05eq) of aluminum trichloride, and 22.3kg ( 1.5eq), add the above-mentioned Grignard reagent o-fluorophenylmagnesium bromide dropwise under temperature control at 5±2°C, and react at this temperature for 3 hours after dropping;

[0034] (3) After the reaction is completed, extract, wash the organic phase with brine, and concentrate to obtain the product o-fluoropropiophenone 14.1k...

Embodiment 3

[0037] A kind of preparation 2,3-difluorobutyrophenone The method is characterized in that the specific preparation steps are as follows:

[0038] (1) Add 237kg (8vol) of methyl tert-butyl ether and 9kg (1.8eq) of magnesium powder into a 1000L reactor, and dropwise add methyl tert-butyl ether containing 40kg of the main raw material 2,3-difluorobromobenzene ( 4vol) solution 159kg, prepared Grignard reagent 2,3-difluorophenylmagnesium bromide;

[0039] (2) Add 207kg (7vol) of methyl tert-butyl ether, 1.8kg (0.1eq) of manganese dioxide, 2.7kg (0.1eq) of aluminum trichloride, and 82kg (2.5eq) of butyric anhydride to another 1000L reactor. ), add the above-mentioned Grignard reagent 2,3-difluorophenylmagnesium bromide dropwise under temperature control at 15±2°C, and react at this temperature for 6 hours after dropping;

[0040] (3) After the reaction is complete, extract, wash the organic phase with brine, and concentrate to obtain the product 2,3-difluorobutyrophenone 30.4k...

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Abstract

The invention relates to a method for preparing fluorine-containing substituted phenyl ketone. Commercial raw materials or easily prepared fluoro bromobenzene is selected as an initial raw material and is converted into a Grignard reagent, and the Grignard reagent is reacted with anhydride under the catalysis of a metal catalyst and Lewis acid to form the fluorine-containing substituted phenyl ketone, wherein R refers to -CH2CnH(2n+1) (n is equal to 0, 1, 2, 3, 4 and 5), fluorine is at an ortho-position, a meta-position, a para-position, 2 and 4 positions, 2 and 3 positions and 3 and 5 positions. By the method, the raw materials are readily available, the purity and yield are high in reaction, process conditions are stable, the operation is simple, the pollution is light, the method has been used for large-scale production, and the invention provides a new idea and method for preparing the fluorine-containing substituted phenyl ketone.

Description

(1) Technical field: [0001] The invention relates to a method for preparing halogenated phenyl ketones, in particular to a method for preparing fluorine-containing substituted phenyl ketones. (2) Background technology: [0002] Halogenated phenylketone is an important pharmaceutical intermediate, mainly used in the preparation of new halogenated piroxacid antibacterial drugs, cardiovascular drugs and antibacterial and anti-inflammatory drugs, such as difluoropropiophenone for the prevention or treatment of ventricular or Supraventricular ectopic beat, ventricular or supraventricular tachycardia, pre-excitation syndrome, ventricular fibrillation after cardioversion, etc., have good curative effect on arrhythmia caused by coronary heart disease and hypertension. Azole derivatives have excellent antifungal effects and high safety, and are suitable for treating fungal infections; polyhalogenated acetophenones are widely used to synthesize various quinolone antibacterial drugs, 2...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/807C07C45/45
Inventor 洪浩韦建李楠
Owner ASYMCHEM LAB TIANJIN
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