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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 preparing halogenated phenyl ketones, can solve the problems of long and complicated operation, instability, harsh reaction temperature control, etc., and achieves a simple process, high conversion rate and mild conditions. Effect

Active Publication Date: 2012-06-20
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
  • 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 tetrahydrofuran (THF) and 28kg (1.4eq) of magnesium powder to a 2000L reactor, and dropwise add 445kg of tetrahydrofuran (2vol) solution containing 160kg of main raw material 3,5-difluorobromobenzene to prepare the Grignard reagent 3,5-Difluorophenylmagnesium bromide;

[0027] (2) Add 427kg (3vol) of THF, 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. 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 completed, extract, wash the organic phase with brine, and concentrate to obtain the product 3,5-difluoroacetophenone 106kg, yield 82.0%, gas chromatography purity (GC) 99.8%. ...

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 2-methyltetrahydrofuran 34.4kg (2vol) successively in another 300L reactor, iron trichloride 0.9kg (0.05eq), aluminum trichloride 0.8kg (0.05eq), propionic anhydride 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 obt...

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 methyl tert-butyl ether 237kg (8vol) in 1000L reactor, magnesium powder 9kg (1.8eq), add dropwise the methyl tert-butyl ether containing main raw material 2,3-difluorobromobenzene 40kg ( 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 completed, extract, wash the organic phase with brine, and concentrate to obtain the product 2,3-difluorobutyrophenone 30.4kg, yield 79.9%, gas ...

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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. (two) 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,...

Claims

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Application Information

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