Hydroxyamine hydrochloride → 5-Bromo-2-propoxybenzonitrile

Participants

Reaction Steps

In formic acid (110 ml) was dissolved 5-bromo-2-propoxybenzaldehyde (21.8 g). To the mixture was added hydroxylamine hydrochloride (9.4 g), and the mixture was refluxed for 7 hours and cooled to room temperature. Under reduced pressure, the solvent was evaporated, and the residue was added to 1N potassium hydroxide. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give 5-bromo-2-propoxybenzonitrile (15.8 g).

Provenance & Evidence