Benzyl Chloride → 4-Benzyloxy-3-chloroaniline

Participants

Reaction Steps

To 4-amino-2-chlorophenol (17.24 g, 50 mmol) dissolved in acetone (250 mL) was added potassium carbonate (6.93 g, 50 mmol) followed by addition of benzyl chloride (5.8 mL, 50 mmol), TBAB (1.64 g, 50 mmol) and potassium hydroxide (2.83 g, 5 mmol). The reaction mixture is allowed to stir at reflux overnight under nitrogen. The reaction mixture was filtered and extracted 3 times with dichloromethane. The combined organic layers were washed two times with 10% NaOH, washed one time with brine, dried over potassium carbonate and then filtered. The sample was concentrated on the rotary evaporator and the resulting oil was dried overnight under vacuum. Flash column chromatography (SiO2, 50:50 hexanes:ethyl acetate) yielded a dark brown oil (160a, 7.3 g, 62%); HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 14.6 min, 97.7% purity; MS (TOF MS ES+): m/z 275 (M+CH3CN+H, 100), 234 (M+H, 11.8).

Provenance & Evidence