Azobisisobutyronitrile → 4'-(Bromomethyl)-2-cyanobiphenyl

Participants

Reaction Steps

To a solution of 699 mg (3.62 mmol) of the intermediate obtained in step B in 15 mL of carbon tetrachloride under nitrogen was added 708.3 mg (3.98 mmol, 1.1 eq) of N-bromosuccinimide and 59 mg (0.36 mmol, 0.1 eq) of azobisisobutyronitrile (AIBN). The resulting mixture was heated in the dark for 4 hours. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum to afford 948 mg (96%) of the product as a yellow solid. 1H NMR (200MHz,CDCl3): 4.51 (s,2H), 7.25-7.80 (m,8H). FAB-MS: calculated for C14H10BrN 272; found 272,274 (M+). 1H NMR indicates the presence of minor amounts of starting material and dibromo derivative.

Provenance & Evidence