Sulfuryl chloride → 2-Chloro-5-fluoro-1,3-benzothiazole

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Reaction Steps

Sulfuryl chloride (0.3 mL, 4.41 mmol) was added neat to 5-fluoro-benzothiazole-2-thiol (680 mg, 3.67 mmol). The mixture was stirred at RT for 1 hour, and then heated to 60° C. for 40 mins. The resulting solution was cooled to room temperature, and poured onto ice, extracted with EtOAc (3×50 mL), washed with brine and dried over Na2SO4. The dried organic layers were concentrated to give 2-chloro-5-fluorobenzo[d]thiazole (520 mg, 2.75 mmol, 75%). ESI-MS (M+1): 187 calc. for C7H5ClFN4S 186.

Provenance & Evidence