Hydrochloric Acid → 2-(4-Bromo-2-fluorophenyl)-2-methylpropanal

Participants

Reaction Steps

To a solution of 2-(4-bromo-2-fluorophenyl)-2-methylpropanenitrile (2.0 g, 8.3 mmol) in THF (20 mL) under nitrogen was added DIBAL-H (19 mL, 19 mmol, 1.0M in THF) dropwise at −30° C. The resulting solution was stirred at ambient temperature for 3 hours before the addition of 2 N aqueous HCl (10 mL) at 0° C. The mixture was stirred at ambient temperature for 10 minutes, then the solution was carefully basified with saturated aqueous NaHCO3 to pH 8-9, and then extracted with EtOAc (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 1-2% EtOAc/hexane) to afford the title compound) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 9.58 (s, 1H), 7.32-7.21 (m, 1H), 7.18-7.03 (m, 2H), 1.41 (s, 6H). MS ESI: [M+H]+ m/z 245.

Provenance & Evidence