Methanol → 4-(Naphthalen-1-yl(phenyl)amino)phenol

Participants

Reaction Steps

To a solution of Compound 5 (2.58 g, 7.93 mmol) in DCM (50 mL) was slowly added BBr3 (8.5 mL, 8.5 mmol) at about −78° C. The resulting mixture was stirred overnight under argon while slowly warming up to room temperature. Methanol (60 mL) was added into the flask, and the mixture was stirred for about 3 hours. After concentration to 20 mL, the mixture was poured into DCM (200 mL), then washed with water, brine, and dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes/ethyl acetate 8:1 to 3:1). The desired fraction was concentrated to give a white solid (Compound 6) (1.84 g, in 77% yield).

Provenance & Evidence