3-Bromo-4-methoxybenzonitrile → (3-Bromo-4-methoxyphenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

Borane-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran. 250 ml) was added to a solution of 2-bromo-4-cyanoanisole (17 g) in tetrahydrofuran (150 ml). The mixture was heated at reflux for 2 hours then cooled to -10° C. and carefully quenched with 6N HCl (130 ml). The mixture was basified with 4N NaOH then extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography, eluting with 120:8:1 dichloromethane:methanol:ammonia, to give the title compound (12.3 g, 71%); δH (250MHz, CDCl3) 3.80 (2H, s, CH2NH2), 3.92 (3H, s, ArOCH3), 6.85 (1H, d, J 8.4Hz, 6-H), 7.20 (1H, dd, J 8.4, 2.1Hz, 5-H), 7.51 (1H, d, J 2.1Hz, 3-H).

Provenance & Evidence