Water → 5-Bromo-2-[(2R)-oxiran-2-ylmethoxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-hydroxybenzaldehyde (68.75 g), (R)-glycidyl 4-toluenesulphonate (65 g) and potassium carbonate (47.3 g) in dry dimethylformamide (1.5 L) was stirred and heated at 60° C. under nitrogen for 24 hours, then cooled and allowed to stand at ambient temperature for 24 hours. The mixture was poured into water (2 L) then extracted with ether (4×400 ml). The combined extracts were washed with brine (4×500 ml), dried over magnesium sulphate, and the solvent removed in vacuo to give an oil which was purified by flash chromatography over silica eluting with a 4:1 mixture of petroleum ether (b.p. 60-80° C.) and ethyl acetate. Appropriate fractions were combined and the solvent removed in vacuo to give an oil, which on trituration with ether (150 ml) gave (R)-5-bromo-2-(2,3-epoxypropoxy)benzaldehyde as a colourless solid (43.3 g).

Provenance & Evidence