Sodium borohydride → 6-Bromo-2,2-dimethyl-2,3-dihydro-1-benzothiophene-3-ol 1,1-dioxide

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Reaction Steps

A cooled (0° C.) solution of 6-bromo-2,2-dimethyl-1-benzothiophen-3(2H)-one 1,1-dioxide (Intermediate 241; 652 mg; 2.25 mmol) in MeOH (15 ml) and DCM (7 ml) was treated with NaBH4 (43 mg; 1.13 mmol) portionwise. The resulting solution was stirred at RT for 1.5 h, before being cooled to 0° C. and carefully quenched with water. The mixture was concentrated under reduced pressure, water was added to the residue and the aqueous phase was extracted three times with DCM. The combined organic phases were washed with brine, dried with MgSO4, filtered and concentrated to dryness to give the title compound as a white solid (637 mg, 97%).

Provenance & Evidence