Azobisisobutyronitrile → 2-(Bromomethyl)-1,3-benzothiazole

Participants

Reaction Steps

A mixture of 2-methylbenzothiazole (2.0 g, 13.40 mmol), N-bromosuccinimide (2.39 g, 13.40 mmol), and AIBN (0.5 g, 3.04 mmol) in CCl4 (40 mL) was refluxed for 12 h, then the mixture was cooled and filtered. The filtrate was concentrated and purified by silica gel chromatography (5% EtOAc/hexane) to give the title compound (2.19 g, 72%) as a yellow oil: 1H NMR (250 MHz, DMSO-d6): δ 5.12 (s, 2H), 7.5 (m, 2H), 8.01 (dd, J=7.9, 1.8 Hz, 1H), 8.15 (dd, J=7.9, 1.8 Hz 1H).

Provenance & Evidence