Boron tribromide → 5-Hydroxynaphthalene-1-carbonitrile

Participants

Reaction Steps

To a solution of 5-methoxynaphthalene-1-carbonitrile (Preparation 11) (880 mg, 4.80 mmol) in DCM (10 mL) under argon at 0° C. was added 1M BBr3 solution in DCM (12.5 mL). After 10 min the mixture was maintained at rt for 4 h. The mixture was partitioned between NaHCO3 solution and EtOAc, the organic phase was washed with 1M HCl, brine and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (isohexane:EtOAc, 2:1) to give the title compound: δH (CD3OD): 6.97 (1H, d), 7.50, 7.52 (2H, 2dd), 7.62 (1H, d), 7.94 (1H, d), 8.53 (1H, d).

Provenance & Evidence