Clean and high-conversion-rate preparing method of 2,2,2-trifluroacetophenone

A trifluoroacetophenone, high conversion technology, applied in the preparation of organic compounds, the preparation of carbon-based compounds, chemical instruments and methods, etc., can solve the problems of low yield, difficult handling, high solvent toxicity, etc. Good selectivity, reduce the generation of impurities, and improve the effect of nucleophilicity

Inactive Publication Date: 2018-05-18
GUANGXI WANDE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages: intense heat release, low yield
Disadvantages: The solvent is highly toxic, AlCl3 is difficult to handle, the strong acid and alkali used corrode equipment and pollute the environment
Disadvantages, there are impurities, the yield is not high

Method used

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  • Clean and high-conversion-rate preparing method of 2,2,2-trifluroacetophenone
  • Clean and high-conversion-rate preparing method of 2,2,2-trifluroacetophenone

Examples

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Embodiment 1

[0026] Such as figure 1 The preparation method of described 2,2,2-trifluoroacetophenone clean high conversion rate, comprises the following steps:

[0027] S1. Add 1mol (97.5g) N,O-dimethyl hydroxylamine hydrochloride, 1mol (149.1g) triethanolamine, 600ml dichloromethane into the reaction vessel, and stir the reaction for 1h at room temperature to obtain free N,O- Dimethylhydroxylamine;

[0028] S2. At 0°C, add dropwise 150ml of dichloromethane solution containing 1mol (210g) trifluoroacetic anhydride to the free N,O-dimethylhydroxylamine obtained in step 2, dropwise for 1.5h, keep warm and continue the reaction 1.5h, after the reaction was completed, add 200ml of water to dilute and separate the layers. After the aqueous phase was washed twice with 300ml of dichloromethane solution, the organic layer was combined, and the organic layer was washed twice with 400ml of water and dried over anhydrous sodium sulfate. Recover to dryness at -35°C to obtain N,O-dimethyltrifluoroami...

Embodiment 2

[0033] Such as figure 1 The preparation method of described 2,2,2-trifluoroacetophenone with clean and high conversion rate is characterized in that it comprises the following steps:

[0034] S1. Add 1mol (97.5g) N,O-dimethyl hydroxylamine hydrochloride, 1.05mol (194.5g) tri-n-butylamine, 600ml dichloromethane into the reaction vessel, stir and react for 2h at room temperature to obtain free N , O-dimethylhydroxylamine;

[0035] S2. At 15°C, add 1.03mol (215g) of trifluoroacetic anhydride in 150ml of dichloromethane dropwise to the free N,O-dimethylhydroxylamine obtained in step 2. Add dropwise for 1 hour, and keep warm for 1 hour. After the reaction, add 200ml of water to dilute and separate layers. After the aqueous phase is washed twice with 300ml of dichloromethane solution, the organic layer is combined, and the organic layer is washed twice with 400ml of water and dried over anhydrous sodium sulfate. Recover to dryness at ℃ to obtain N, O-dimethyl trifluoroamide to be ...

Embodiment 3

[0040] Such as figure 1 The preparation method of described 2,2,2-trifluoroacetophenone clean high conversion rate, comprises the following steps:

[0041]S1. Add 1 mol (97.5 g) N, O-dimethyl hydroxylamine hydrochloride, 1.02 (152.5 g) mol triethanolamine, 600 ml dichloromethane into the reaction vessel, and stir the reaction for 1 h at room temperature to obtain free N, O - Dimethylhydroxylamine;

[0042] S2. At 0°C, add 1.05mol (220g) of trifluoroacetic anhydride in 150ml of dichloromethane dropwise to the free N,O-dimethylhydroxylamine obtained in step 2, dropwise for 1.5h, and keep warm to continue the reaction 2h, after the reaction is over, add 200ml of water to dilute and separate the layers. After the aqueous phase is washed twice with 300ml of dichloromethane solution, the organic layer is combined, and the organic layer is washed twice with 400ml of water and dried over anhydrous sodium sulfate. Recover to dryness at 35°C to obtain N,O-dimethyltrifluoroamide to be ...

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Abstract

The invention discloses a clean and high-conversion-rate preparing method of 2,2,2-trifluroacetophenone. The method includes the following steps of S1, making N,O-dimethylhydroxylamine hydrochloride as the raw material react with organic alkali to obtain free N,O-dimethylhydroxylamine; S2, making trifluoroacetic anhydride react with free N,O-dimethylhydroxylamine to generate N,O-dimethyltrifluoroacetamide; S3, making a Grignard reagent react with N,O-dimethyltrifluoroacetamide to prepare trifluroacetophenone, recovering N,O-dimethylhydroxylamine generated in the step S1, applying N,O-dimethylhydroxylamine to the step S2, and recycling the reaction solvents used in the steps S1, S2 and S3. By means of the preparing method, prepared high-nucleophilicity N,O-dimethyltrifluoroacetamide reactswith the Grignard reagent, 2,2,2-trifluroacetophenone is efficiently prepared, meanwhile produced byproducts can be applied for preparing N,O-dimethyltrifluoroacetamide, and a recycling effect is achieved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a clean and high-conversion preparation method of 2,2,2-trifluoroacetophenone. Background technique [0002] 2,2,2-trifluoroacetophenone is a commonly used chemical reagent, and the commonly used synthetic methods of 2,2,2-trifluoroacetophenone are: (1) trifluoroacetic acid directly reacts with the Grignard reagent of bromobenzene, One-step direct synthesis. The yield is about 60%. The method has the advantages of simple operation and cheap raw materials. Disadvantages: Excessive heat release and low yield. (2) At -40°C, in carbon disulfide solvent, under the action of Lewis acid AlCl3, trifluoroacetic anhydride and benzene ring are produced by Friedel-Crafts acylation reaction, and the yield is about 70%. Advantages of the method: one-step synthesis. Disadvantages: The solvent is highly toxic, AlCl3 is difficult to handle, and the strong acid and alkali used co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/80C07C45/00C07C239/20
CPCC07C45/004C07C239/20C07C49/80
Inventor 蒋青锋杨坤杨正业蒋华容
Owner GUANGXI WANDE PHARMA
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