Boron tribromide → 2-(4-Hydroxyphenyl)-1H-indol-5-ol

Participants

Reaction Conditions

Reaction Steps

Five g (18.7 mmol) of 5-methoxy 2-(4 methoxyphenyl)indole was dissolved in 30 mL CH2Cl2 under argon, cooled on dry ice/acetone and 70 mL 1 M BBr3 were added with stirring. The solution was warmed to 0° C. for 30 min. It was then stirred at room temperature overnight. The reaction mixture was suspended in sat. NaHCO3 solution and extracted with CH2Cl2 (2×). The organic extract was washed with brine and dried over Na2SO4. Removal of the solvent in vacuo and flash chromatography (5% MeOH in CH2Cl2) gave 3.33 g of 3.

Provenance & Evidence