Water → 7-Hydroxynaphthalene-2-carbonitrile

Participants

Reaction Steps

A solution of BBr3 (840 μL, 8.8 mmol) in CH2Cl2 (4 mL) is added to a solution of 7-methoxy-2-naphthonitrile (646 mg, 3.53 mmol) in CH2Cl2 (6 mL). The reaction is allowed to stir for 30 hours. Water (about 5 mL) is slowly added. The pH is adjusted to 7 with saturated Na2CO3 then the mixture is extracted with CH2Cl2. The combined organic layers are dried (Na2SO4), filtered and concentrated to dryness. The crude material is purified by column chromatography (step gradient of 1% MeOH in CH2Cl2 to 5% MeOH in CH2Cl12) to give 7-hydroxy-2-naphthonitrile as a white solid (477 mg, 80%). HRMS (EI) calculated for C11H7NO: 169.0528, found 169.0527.

Provenance & Evidence