Methanol → 3-Bromo-2-hydroxybenzaldehyde

Participants

Reaction Steps

Over 0.25 hours 2-bromophenol (22.38 g, 129 mmol) was added to a solution of Mg(OMe)2 in methanol (111.9 ml, 8% w/w) and toluene (35 ml). The reaction was heated to reflux and maintained at reflux for 1 hour, then toluene (118 ml) was added. The solvent was distilled off until the temperature reached 92-94° C. A solution of paraformaldehyde in toluene was added portionwise over 1 hour at 80-90° C. and the reaction mixture heated to reflux and maintained at reflux for 3 hours. The reaction mixture was then allowed to cool to ambient temperature and left to stand overnight. Toluene (140 ml) was added to the reaction mixture, which was then washed with 2M H2SO4 (140 ml). The organic phase was dried and evaporated and the crude material used in the next step without further purification.

Provenance & Evidence