Dichloromethane → 4-(Bromomethyl)-2-hydroxybenzonitrile

Participants

Reaction Steps

2-hydroxy-4-hydroxymethylbenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL) and CH2Cl2(5 mL) and then treated with triphenylphosphine (0.53 g, 2.01 mmol) and carbon tetrabromide (0.67 g, 2.01 mmol) at ambient temperature with stirring. After 2 h, the reaction mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), the organic layer were separated, dried (MgSO4), and filtered to give the title compound after silica gel chromatography (15% EtOAc/hexane to 25% EtOAc/hexane).

Provenance & Evidence