4-Methoxybenzylamine → N-(4-methoxybenzyl)(5-bromo-2-nitrophenyl)methanamine

Participants

Reaction Steps

To a stirring mixture of 5-bromo-2-nitrobenzaldehyde (0.46 g, 2.0 mmole (prepared according to a reference: Organic Letters (2003), 5(13), 2251-2253) in DCM (4.0 mL) was added p-methoxybenzyl amine (0.32 mL, 2.4 mmol) and three drops of AcOH. The mixture was stirred at RT for 5 min, after which was added NaB(OAc)3H (0.64 g, 3 mmol) and the entire mixture was stirred for additional 2 hrs. The reaction mixture was quenched with NaHCO3 (aq) and diluted with EtOAc (10 mL). The separated aqueous layer was extracted with EtOAc (2×15 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a crude residue, which was purified using flash column chromatography (100% hexane to 30% EtOAc/hexanes gradient) to obtain the desired product N-(4-methoxybenzyl)(5-bromo-2-nitrophenyl)methanamine as a pale yellow oil. MS m/e 351 (M+H)+.

Provenance & Evidence