Azobisisobutyronitrile → 5-(Bromomethyl)-2,1,3-benzothiadiazole

Participants

Reaction Steps

5-Methylbenzo-2,1,3-thiadiazole (5 g, 33.3 mmol) in CHCl3 (75 mL) was treated with N-bromosuccinimide (5.32 g, 33.3 mmol) and a catalytic amount of AIBN and heated at reflux for 16 hours. After cooling to ambient temperature, the resulting precipitate was fitered off and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to provide 4.8 g of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.62 (s, 2H), 7.65 (dd, 1H), 8.0 (m, 2H).

Provenance & Evidence