Acetic Acid → 4'-Fluoro-2-(4-trifluoromethylphenyl)acetophenone

HRID 1975656

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(O)(=[O:22])C.S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 12.2 g (46 mmol) of 4-fluoro-4'-trifluoromethyltolane, 60 ml of water, 60 ml of acetic acid, 40 ml of sulfuric acid and 13.6 g (46 mmol) of mercuric sulfate were added, and the mixture was stirred at 90° C. for 3.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9) to obtain 5.1 g of 4'-fluoro-2- (4-trifluoromethylphenyl)acetophenone having a melting point of from 87° to 89° C.

Workup

additionwas added to the reaction mixture
extractionthe mixture was extracted with diethyl ether
dry with materialThe extract was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off
customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record: ord-09fb09a549d346f4add477d5cea47913
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05288727

Linked notes

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