Benzoyl Peroxide → 2-(Bromomethyl)-5-fluorobenzo[d]thiazole

Reaction equation

C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=2[N:24]=1.[Br:30]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=2[N:24]=1

Participants

Procedure

127 mg of dibenzoyl peroxide were added to a solution of 8.79 g of 2-methyl-5-fluorobenzothiazole and 20.6 g of N-bromosuccinimide in 88 ml of carbon tetrachloride at room temperature and the resulting mixture was stirred under reflux for 6 hours. At the end of this time, the reaction mixture was filtered and the resulting filtrate was concentrated by evaporation under reduced pressure to give a crude crystalline solid which was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate to give 850 mg (yield 7%) of the title compound as a solid.