Azobisisobutyronitrile → [2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromide

Participants

Reaction Steps

To a solution of 5.0 g (16.5 mmol) of 4-methyl-2'-(t-butylaminosulfonyl)-1,1'-biphenyl in 400 mL of carbon tetrachloride was added 2.35 g (13.2 mmol, 0.8eq) of recrystallized N-bromosuccinimide and 27.5 mg of azobisisobutyronitrile (AIBN). The mixture was refluxed under a nitrogen amosphere for 4 hours at which time an additional 1.17 g (6.57 mmol, 0.40 eq) of N-bromosuccinimide and a trace of AIBN were added and refluxing continued for another 2 hours. The mixture was cooled to room temperature, filtered and the filtrate concentrated to dryness to give 7.11 g of crude product which was used without further purification. 1H NMR (200 MHz, CDCl3): δ 1.07 (s, 9H), 3.63 (br s, 1H), 4.60 (s, 2H), 7.3-7.7 (m,7H), 8.11 (dd; 2, 8 Hz; 1H). FAB-MS: calculated for C17H20BrNO2S 381; found 382 (M+H, 2.5%).

Provenance & Evidence