A method for preparing trifluoromethyl acetophenone compound

A technology of trifluoromethyl acetophenone and trifluoromethyl halogenated benzene, which is applied in the field of preparation of trifluoromethyl acetophenone compounds, can solve the problems of expensive starting materials, low yield, easy diazomethane Explosion and other problems, to achieve the effect of novel preparation process, high product purity, and less environmental pollution

Inactive Publication Date: 2008-04-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among the four synthetic methods, some reaction starting materials are expensive, difficult to source, and low yield, and the cadmium reagent used in method 2 will increase the treatment work of wastewater, and the diazomethane in method 3 is explosive and highly toxic. It is difficult to carry out large-scale industrial production, and the recovery of organic amines in the Heck reaction of method 4 still needs to be solved

Method used

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  • A method for preparing trifluoromethyl acetophenone compound
  • A method for preparing trifluoromethyl acetophenone compound
  • A method for preparing trifluoromethyl acetophenone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: the preparation of m-trifluoromethyl acetophenone

[0021] 0.18 g (1 mmol) of m-trifluoromethyl chlorobenzene, 0.5 g (5 mmol) of vinyl butyl ether, 0.0012 g (0.005 mmol) of palladium acetate, 0.3 g (1.5 mmol) of Styrene-DVB (D301 R) resin millimoles), 10 ml of dimethyl sulfoxide, placed in a 200 ml three-necked flask, stirred and heated, and reacted at 100° C. for 1 hour. After the reaction, cool, add 10% dilute hydrochloric acid to acidify to pH=3, stir for 30 minutes, extract with toluene (3×50 ml) (extract 3 times, 50 ml each time, the same below), dry the extract, and concentrate , 0.095 g of the product was separated by column chromatography, and the yield was 50%. Boiling point 198~202℃, purity ≥98%, MS(m / z): 188(M + ).

Embodiment 2

[0022] Embodiment 2: the preparation of m-trifluoromethyl acetophenone

[0023] 0.22 g (1 mmol) of m-trifluoromethyl bromide, 0.2 g (2 mmol) of vinyl butyl ether, 0.0012 g (0.005 mmol) of palladium acetate, 0.4 g (2 mmol) of Styrene-DVB (D301 R) resin millimoles), 100 milliliters of dimethylformamide were placed in a 200 milliliter three-necked flask, stirred and heated, and reacted at 150° C. for 10 hours. After the reaction, cool, add 10% dilute hydrochloric acid to acidify to pH=3, stir for 30 minutes, extract with toluene (3×50 ml), dry the extract, concentrate, and separate by column chromatography to obtain 0.13 g of the product, with a yield of 70 %. Boiling point 198~202℃, purity ≥98%, MS(m / z): 188(M + ).

Embodiment 3

[0024] Embodiment 3: the preparation of p-trifluoromethylacetophenone

[0025] 0.22 g (1 mmol) of p-trifluoromethylbromobenzene, 0.2 g (2 mmol) of vinyl butyl ether, 0.0012 g (0.005 mmol) of palladium acetate, 0.3 g (1.5 mmol) of Styrene-DVB (D301 R) resin millimoles), 50 milliliters of 1-methylpyrrolidone were placed in a 200 milliliter three-necked flask, stirred and heated, and reacted at 50° C. for 50 hours. After the reaction, cool, add 10% dilute hydrochloric acid to acidify to pH=3, stir for 30 minutes, extract with toluene (3×50 ml), dry the extract, concentrate, and separate by column chromatography to obtain 0.155 g of the product, with a yield of 80 %. Melting point 30~32℃, purity ≥98%, MS(m / z): 188(M + ).

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Abstract

The present invention provides a preparation method of chemical compound of trifluoromethylhypnone shown by formula (I), the method includes that: trifluoromethylphenyl halides shown in formula (II) and ethenyl-ethers type shown in form (III) are adopted as the raw material , reaction is carried out for 1-50 hours under agitation under 50 DEG C to 150 DEG C in an apolar aprotic solvent, with the presence of catalyst of palladium acetate and macroporous alkalescence styrene anion-exchange resin shown in form(IV) , after the reaction, the reaction liquid is isolated and purified to obtain the chemical compound of trifluoromethylhypnone; the preparation method has novel technicst, low cost, easy operation, recyclable resin, with minor environmental pollution because of absence of organic phosphine ligands, little molecular organic amine and inorganic alkali.

Description

(1) Technical field [0001] The present invention relates to a kind of preparation method of trifluoromethyl acetophenone compound, especially a kind of macroporous weak basic styrene series anion exchange resin as solid base, palladium acetate as catalyst, in the absence of organic phosphine ligand and small The invention discloses a method for preparing trifluoromethyl acetophenone compound by reacting halogenated aromatic hydrocarbon and vinyl ether compound under the condition of molecular organic amine or inorganic base by using Heck reaction. (2) Background technology [0002] Trifluoromethyl acetophenone compound is a class of important pharmaceutical intermediates, widely used in medicine, pesticide, chemical industry and other fields. The preparation of current trifluoromethyl acetophenone compound mainly contains: 1, the Grignard reaction of trifluoromethyl benzonitrile and methyl iodide; Reagent reaction; 3. Reaction of trifluoromethylbenzaldehyde and diazomethane...

Claims

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Application Information

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IPC IPC(8): C07C49/80C07C45/45C07C45/00B01J31/06B01J31/08
Inventor 裴文王菊华吴香梅王勤沈忱
Owner ZHEJIANG UNIV OF TECH
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