Carbon tetrabromide → 4-(Bromomethyl)-2-hydroxybenzonitrile

Participants

Reaction Steps

2-Hydroxy-4-hydroxymethylbenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL)—CH2Cl2(5 mL) and 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)—H2O (100 mL), the organic layer separated, dried (MgSO4), and filtered to give the title compound after silica gel chromatography (15% EtOAc/hexane to 25% EtOAc/hexane).

Provenance & Evidence