4-Bromobenzenesulfonamide → 4-[2-(4-Chlorophenyl)phenyl]benzenesulfonamide

Participants

Reaction Steps

Following the general procedure outlined in Synthetic Scheme IX, 1.6 g (6.9 mmol) of 2-(4-chlorophenyl)phenylboronic acid (Step 2) was reacted with 1.8 g (7.6 mmol) of 4-bromobenzenesulfonamide. Purification by silica gel chromatography (Waters LC-2000) with ethyl acetate/hexane (3:7) and subsequent recrystallization from ethyl acetate/hexane gave 1.59 g (67%) of 4-(2-(4-chlorophenyl)phenyl]benzenesulfonamide as a colorless solid: mp 206.2-207.0° C.; NMR (CDCl3) δ 4.77 (s, 2H), 7.04 (d, J=9 Hz, 2H), 7.16-7.31 (m, 4H), 7.36-7.51 (m, 4H), 7.80 (d, J=9 Hz, 2H). MS (EI): m/e (rel intensity) 343 (100), 308 (13), 262 (21), 228 (82); HRMS Calc'd for C18H14ClNO2S: 343.0434. Found: 343.0434. Anal. Calc'd for C18 H14ClNO2S: C, 62.88; H, 4.10; N, 4.07. Found: C, 62.66; H, 4.36; N, 4.09.

Provenance & Evidence