Water → 6-Fluorosalicylaldehyde

Participants

Reaction Steps

A solution of boron tribromide in dichloromethane (1M; 20.15 ml) was added dropwise to a stirring solution of 2-fluoro-6-methoxybenzaldehyde (4.66 g, prepared as described above) in dichloromethane (40 ml) at -78° C. The mixture was allowed to warm to ambient temperature then water (150 ml) was added and the mixture extracted with dichloromethane (3×100 ml). The combined extracts were washed with water (100 ml) then brine (100 ml) and the solvent evaporated. Distillation of the residue at reduced pressure gave 2-fluoro-6-hydroxybenzaldehyde (2.0 g), contaminated with 7% of the starting methoxy compound, as an oil b.p. 60° C. at 4.66 mbar, which was used without further purification.

Provenance & Evidence