A method for preparing 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione

A technology of p-methylphenyl and p-methylacetophenone, which is applied in the field of fluorine compound preparation, can solve the problems of long reaction time, environmental pollution, and complicated acidification steps in the post-treatment process, etc.

Active Publication Date: 2021-04-02
ZHEJIANG LANTIAN ENVIRONMENTAL PROTECTION HI TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction time of this method is as long as 24 hours, and the post-treatment process is complicated and must use an acidification step. Excessive use of ethyl trifluoroacetate will easily cause environmental pollution

Method used

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  • A method for preparing 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione
  • A method for preparing 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione
  • A method for preparing 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 1000 mL three-necked flask, add 500 mL of ether, add 68.0 g (1.0 mol) of sodium ethoxide and 134 g (1.0 mol) of p-methylacetophenone under stirring, heat the reaction to 40 ° C, and after 6 hours of reaction, distill off the solvent. A yellow solid was obtained, which was partially dissolved by adding 300ml of acetonitrile, and 230.1g (1.3mol) of trifluoroacetyl bromide was introduced into the reaction solution, reacted at 50°C for 3h, and the filtrate was obtained by suction filtration, part of the acetonitrile was distilled off, and 210g of a white solid was obtained at -10°C , the content is 99.2%, and the yield is 91.2%.

Embodiment 2

[0030] In a 1000mL three-necked flask, add 500mL of isopropyl ether, add 81g (1.5mol) of sodium methylate and 134g (1.0mol) of p-methylacetophenone under stirring, and heat the reaction to 30°C. After 6 hours of reaction, evaporate the solvent , add 250ml of m-dichlorobenzene to partially dissolve, pass 127.6g (1.1mol) trifluoroacetyl fluoride into the reaction solution, react at 40°C for 2h, obtain the filtrate by suction filtration, distill off part of m-dichlorobenzene, and obtain white The solid is 212g, the content is 99.0%, and the yield is 92.2%.

Embodiment 3

[0032] In a 1000mL three-necked flask, add 500mL of toluene, add 50.5g (0.5mol) of triethylamine and 134g (1mol) of p-methylacetophenone under stirring, and pass 135.3g (1.1mol) of trifluoroacetyl chloride into the reaction solution , reacted at 20°C for 6h, obtained the filtrate by suction filtration, evaporated part of the toluene, and obtained 208g of white solid at -10°C, the content was 99.2%, and the yield was 90.4%.

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Abstract

The invention provides a method for preparing 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione. The method comprises the step of reacting by virtue of trifluoroacetyl halide and p-methylacetophenone in an organic solvent under the action of a catalyst, so as to obtain 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione and / or an enol formisomer of 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione. The method provided by the invention has the advantages of low raw material cost, mild reaction conditions, low environmental pollution and suitability in industrial production.

Description

technical field [0001] The invention belongs to the field of fluorine compound preparation, and in particular relates to a preparation method of 1-p-methylphenyl-4,4,4-trifluoro-1,3-butanedione. Background technique [0002] Celecoxib was developed by GD Searle Company of the United States and was first launched in the United States in 1998. It is the first selective non-steroidal anti-inflammatory analgesic drug, which can effectively treat a variety of common clinical acute pains, as well as chronic pains. 1-p-methylphenyl-4,4,4-trifluorobutan-1,3-dione is an important intermediate for the synthesis of celecoxib, and its preparation method is reported as follows: [0003] Penning et al. reported in J.Med Chem.1997.40 (9): 1347-1365. In an organic solvent, p-methylacetophenone and ethyl trifluoroacetate carried out Claisen condensation under the effect of 25% sodium methylate-methanol to obtain Method for 1-p-methylphenyl-4,4,4-trifluorobutan-1,3-dione. After the reaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/72C07C49/76
CPCC07C45/72C07C49/76
Inventor 陈伟李华徐卫国蒋强杨汪松
Owner ZHEJIANG LANTIAN ENVIRONMENTAL PROTECTION HI TECH
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