Boron tribromide → 3-(4-Chloro-benzylamino)-phenol

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (2.59 ml, 27.4 mmol) was added drop wise to a cool stirred solution of (4-chloro-benzyl)-(3-methoxy-phenyl)-amine (2.37 g, 9.6 mmol) in anhydrous dichloromethane (90 ml) and the mixture was stirred at 0° C. for 1 hour then ambient for 15 hours. The reaction was cooled to 0° C. and quenched with the addition of saturated sodium bicarbonate solution (aq) (100 ml). The aqueous layer was collected and extracted further with dichloromethane (2×100 ml) and combined organic extracts were concentrated in vacuo to obtain crude product. The crude residue was purified by flash chromatography (SiO2) eluting with 5% ethyl acetate/dichloromethane to yield a cream solid (1.58 g, 71% yield). HPLC retention time 4.55 min Mass spectrum (ES+) m/z 234 (M+H).

Provenance & Evidence