Boron tribromide → 2,3-Dichloro-4-hydroxybenzaldehyde

Participants

Reaction Steps

The title compound was prepared by reacting 2,3-dichloro-4-methoxybenzaldehyde (10 g, 49 mmol) with boron tribromide (147 ml of 1N solution in CH2Cl2, 147 mmol) according to method D to yield 11.3 g dark grey solid which is mainly the designed product indicated by 1H-NMR. It was triturated with 30% CHCl3 in hexane to give 3.6 g of grey solid as pure product. An analytical sample was afforded as white solid by reverse-phase preparative HPLC: mp 176-178° C.; 1H NMR (DMSO-d6): δ 7.10 (1H, d, J=8.68 Hz), 7.74 (1H, d, J=8.67 Hz), 10.16 (1H, s), 11.95 (1H, s); MS (ESI) m/z 189/191/193 (M−H)−, 193/191/195 (M+H)+.

Provenance & Evidence