Methanol → 2-Bromo-6-chloro-3-ethoxy-4-(1-hydroxyethyl)benzonitrile

Participants

Reaction Steps

Sodium tetrahydroborate (38 mg, 0.99 mmol) was added to a mixture of 4-acetyl-2-bromo-6-chloro-3-ethoxybenzonitrile (200 mg, 0.7 mmol) in methanol (5 mL, 100 mmol) at 0° C. The reaction was stirred at room temperature for 1 hour, concentrated and partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated to give crude 2-bromo-6-chloro-3-ethoxy-4-(1-hydroxyethyl)benzonitrile as a clear oil (0.15 gm, 100%), LCMS calculated for C11H11BrClNO2(M+H)+: m/z=303.9, 305.9; found: 304.0, 305.9.

Provenance & Evidence