3-phenylpropanoyl fluoride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of diethylaminosulfinium tetrafluoroborate (750 mg, 3.3 mmol) in dichloromethane (10 mL) at room temperature was added 3-phenylpropanoic acid (245 mg, 1.6 mmol) and triethylamine trihydrofluoride (266 μl, 1.6 mmol). The reaction mixture was stirred for 24 hours, then an aqueous solution of sodium bicarbonate (5%) was added and stirring was continued for 30 minutes. The organic phase was isolated and dried with magnesium sulphate. The solution was diluted with pentane (10 mL) and the solution was passed through a pad of silica gel with pentane elution. Solvent were evaporated in vacuum to provide 3-phenylpropanoyl fluoride (168 mg, 68%) as a clear liquid. 1H NMR (CDCl3, 300 MHz) δ 7.30-7.17 (m, 5H), 2.96 (t, J=7.6 Hz, 2H), 2.79 (t, J=7.6 Hz, 2H); 19F NMR (CDCl3, 282 MHz) δ 44.8 (s, 1F); 13C NMR (CDCl3, 75 MHz) δ 163.0 (d, 1JC-F=180.2 Hz), 139.1, 128.9, 128.5, 127.0, 34.7 (d, =50.7 Hz), 30.2. stirring was continued for 30 minutes The organic phase was isolated dried with magnesium sulphate The solution was diluted with pentane (10 mL) the solution was passed through a pad of silica gel with pentane elution Solvent were evaporated in vacuum