5-Bromo-2-methylbenzothiazole → 5-Bromo-2-(bromomethyl)-1,3-benzothiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Bromo-2-methyl-benzothiazole (1.0 g, 4.385 mmol) in 0014 (15 mL) is added N-bromosuccinamide (1.1 g, 6.140 mmol) and azobisisobutyronitrile (0.029 g, 0.175 mmol) at room temperature reaction. The reaction mixture is heated to 75° C. for 16 hours. Reaction mixture is cooled to room temperature, filtered and the solvent evaporated in vacuo to give the crude material, which is then purified by flash chromatography using 3.5% ethyl acetate in hexane as an eluent to afford the title compound (0.85 g). 1H NMR (400 MHz, DMSO-d6) δ: 5.12 (s, 2H), 7.68-7.71 (dd, J1=1.92 Hz, J2=8.76 Hz, 1H), 7.95 (d, J=8.6 Hz, 1H), 8.43 (d, J=1.92 Hz, 1H). LC-MS (m/z): [M+H]=308.2.

Provenance & Evidence