General Description
3′,5′-Difluoroacetophenone, also known as 1-(3,5-difluorophenyl)ethanone, is a fluorinated acetophenone.
Synthesis
The general procedure for the synthesis of 3,5-difluoroacetophenone from 1-(3,5-difluorophenyl)ethanol was carried out as follows: a solution of Dess-Martin periodontane (9.66 g, 22.8 mmol) was added batchwise to a solution of 1-(3,5-difluorophenyl)ethanol (3.00 g, 19.0 mmol) in dichloromethane (40 mL) under ice-bath cooling conditions. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, the solvent was removed by concentration under reduced pressure. The residue was purified by silica gel column chromatography using a CombiFlash device eluting with a gradient of ethyl acetate/hexane (0-40%). Purification afforded 3,5-difluoroacetophenone (2.06 g, 69.6% yield) as a colorless oil. Its 1H NMR (300 MHz, CDCl3) data were as follows: δ 7.45 (m, 2H), 7.01 (m, 1H), 2.59 (s, 3H) ppm.
