Azobisisobutyronitrile → 4-(2-Bromomethyl-phenyl)-[1,2,3]thiadiazole

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Reaction Steps

A solution of 4-o-tolyl-[1,2,3]thiadiazole (100 mg, 0.57 mmol), N-bromosuccinimide (100 mg, 0.57 mmol) and 2,2′-azobisisobutyronitrile (9.4 mg, 0.057 mmol) in chloroform (10 ml) was heated at reflux temperature for ˜18 h. Additional chloroform was added and the mixture was washed with water, 5% sodium thiosulfate solution and brine. Drying and solvent evaporation gave 4-(2-bromomethyl-phenyl)-[1,2,3]thiadiazole; 1H NMR (CDCl3, 300 MHz) δ8.87 (s, 1H), 7.67-7.39 (m, 4H), 4.71 (s, 2H). cls Step D: 4-(2-Azidomethyl-phenyl)-[1,2,3]thiadiazole (I-13-4)

Provenance & Evidence