Benzoyl Peroxide → 2-(Bromomethyl)-1,3-thiazole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-methyl-thiazole-4-carbonitrile (3.0 g, 24.1 mmol), N-bromosuccinimide (4.3 g, 24.1 mmol) in CCl4 (50 mL) was added benzoyl peroxide (0.583 g, 0.10 mmol). The resulting mixture was stirred at 95° C. for 15 h, concentrated under reduced pressure, diluted with EtOAc (100 mL) and washed with saturated Na2S2O3 (50 mL), NaHCO3 (50 mL) and brine (20 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The crude residue was purified via silica gel column chromatography using EtOAc/n-hexane as eluent to afford the title compound (4.6 g, 83%) as yellow oil. Rf0.39 (silica gel,EtOAc/hexane,3/7).

Provenance & Evidence