N-bromobutanimide → 5-(Bromomethyl)benzo[d]thiazole

Participants

Reaction Steps

A mixture of 5-methylbenzothiazole (5.0 g), N-bromosuccinimide (6.0 g) and carbon tetrachloride (500 ml) was refluxed for 4 hours. Upon cooling, the mixture was evaporated to dryness and the residue chromatographed over silica gel. On elution with a mixture of methylene chloride and hexane (9:1), the title product was obtained as a white solid [0.56 g; NMR(CDCl3,60 MHz): 4.6 (s, 2H), 7.4 (dd, J=7 Hz, 2 Hz, 1H). 7.9 (d, J=7 Hz, 1H), 8.15 (d, J=2 Hz, 1H), 9.0 (s, 1H).

Provenance & Evidence