Benzenesulfonyl chloride → N-[2-(3-bromophenyl)ethyl]benzenesulfonamide

Participants

Reaction Steps

Benzenesulfonyl chloride (1.54 mL, 12.00 mmol) was added to [2-(3-bromophenyl)ethyl]amine (2.00 g, 10.00 mmol) and N,N-di-iso-propylethylamine (5.22 mL, 29.99 mmol) in dichloromethane (33 mL) at 0° C. under argon and the reaction was allowed to warm to room temperature and stirred for 16 hours. The dichloromethane was concentrated under vacuum; diethyl ether was then added, followed by 10% citric acid. The solution was extracted with diethyl ether and the organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 3.22 g (95%) of N-[2-(3-bromophenyl)ethyl]benzenesulfonamide as a solid. 1H NMR (400 MHz, d6-DMSO): δ 7.77-7.73 (m, 2H), 7.70 (t, J=6 Hz, 1H), 7.62 (d, J=7 Hz, 1H), 7.57 (t, J=8 Hz, 2H), 7.40-7.34 (m, 2H), 7.22 (t, J=8 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 2.96 (q, J=7 Hz, 2H), 2.67 (t, J=7 Hz, 2H). ESI-LCMS m/z 340 (M+H)+.

Provenance & Evidence