2-Bromonaphthalene → 5-Bromo-2-hydroxy-alpha-(2-naphthyl)benzyl alcohol

Participants

Reaction Steps

A solution of 5-bromosalicylaldehyde (2 g) in diethyl ether (20 ml) was added to (2-naphthyl)magnesium bromide [prepared by adding a solution of 2-bromonaphthalene in diethyl ether (30 ml) to a mixture of magnesium turnings (0.49 g) and diethyl ether (20 ml) and heating the resultant mixture to reflux for 90 minutes] and the mixture was stirred at ambient temperature for 1 hour. A saturated aqueous ammonium chloride solution (20 ml) was added and the mixture was extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p. 60°-80° C.) and ethyl acetate as eluent to give 5-bromo-2-hydroxy-α-(2-naphthyl)benzyl alcohol (1.98 g, 60%), m.p. 115°-117° C.

Provenance & Evidence