Ethylamine → N-ethyl-4-fluorobenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of ethylamine (69.4 mL, 139 mmol) and triethylamine (21.10 mL, 151 mmol) in DCM (Volume: 150 mL) was added p-fluorobenzoyl chloride (15.13 mL, 126 mmol) at 0° C. The reaction was stirred at 0° C. for 1 hr and then warmed slowly to room temperature. The reaction mixture was diluted with water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered, and the organic phase stripped to dryness via rotary evaporation. The organic extract was dried in vacuo to provide N-ethyl-4-fluorobenzamide (21 g, 100% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12 (t, J=7.20 Hz, 3 H) 3.23-3.32 (m, 2 H) 7.24-7.33 (m, 2 H) 7.87-7.95 (m, 2 H) 8.49 (t, J=3.92 Hz, 1 H). ESI-MS:m/z 168.0 (M+H)+. mp=73.2-76.3° C.

Provenance & Evidence