2-Bromopropane → 3-Bromo-4-(propan-2-yloxy)benzaldehyde

Participants

Reaction Steps

Potassium carbonate (10.28 g, 7.4 mmol) and 2-bromopropane (8.7 ml) were added to 3-bromo-4-hydroxybenzaldehyde (7.46 g, 3.7 mmol) in N,N-dimethylformamide (20 ml). The mixture was stirred at room temperature for 3 hours, then partitioned between ethyl acetate and water. The organic phase was washed with brine and dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (90:10 increasing to 80:20) to give the title compound (5.34 g). 1H NMR (250 MHz, CDCl3) δ 9.82 (1H, s), 8.03 (1H, d, J=2.0 Hz), 7.82-7.78 (1H, dd, J=6.0, 2.0 Hz), 7.00 (1H, d, J=6.0 Hz), 4.72 (1H, septet, J=6.0 Hz), and 1.40 (6H, d, J=6.0 Hz).

Provenance & Evidence