Sodium Bicarbonate → (4-Bromo-2-nitrophenyl)methanol

Participants

Reaction Steps

Borane tetrahydrofuran complex solution (1 M in tetrahydrofuran, 13 mL, 13 mmol) was added over 5 min to a solution of 4-bromo-2-nitrobenzoic acid (2.00 g, 8.13 mmol) at room temperature, then after 72 h the reaction mixture was carefully poured upon sat. aq. sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated to produce (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 96%). White solid, 1H-NMR (300 MHz, CDCl3): 8.25 (d, J=1.8, 1 H), 7.80 (dd, J=8.1, 1.8, 1 H), 7.67 (d, J=8.1, 1 H), 4.96 (d, J=6.3, 2 H), 2.37 (t, J=6.3, 1 H).

Provenance & Evidence