Boron tribromide → 2,4-Dichloro-6-hydroxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide

Participants

Reaction Steps

To a solution of 30 mg (0.06 mmol) of 2,4-dichloro-6-methoxy-N-[2,2,2-trifluoro-1-(1H-indol-3-ylmethyl)ethyl]benzenesulfonamide in 2 mL of dichloromethane was added 1 mL (1 mmol) of 1 M boron tribromide in CH2Cl2. After 1 hour, the reaction was cooled in an ice-water bath and cautiously quenched with 5-10 mL of methanol with stirring. The mixture was warmed to room temperature and the residue was dissolved in ethyl acetate and washed with three 20 mL portions of 1 M aqueous HCl, saturated aqueous sodium bicarbonate solution, and brine. The organic layers was dried over sodium sulfate, decanted, and concentrated in vacuo. The product crystallized upon concentration to afford 4 mg (13%) of the title compound.

Provenance & Evidence