Sodium Bicarbonate → 2-bromo-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide

Participants

Reaction Steps

A solution of 4 g (11 mmol) of 2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide and 35 mL of BBr3/methylene chloride in 200 mL of methylene chloride was stirred for 1 hour, poured into ice-water, made basic with sodium bicarbonate and extracted with methylene chloride. This solution was washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel and eluted with ethyl acetate to give 1.35 g (33% yield) of 2-bromo-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide.

Provenance & Evidence