Acetic Acid → 4-bromo-2-fluoro-N,N-dimethylaniline

Participants

Reaction Steps

To a solution of 2-fluoro-4-bromoaniline (1.0 g, 5.26 mmol) in AcOH (20 mL) at rt was added NaCNBH3 (1.654 g, 26.3 mmol). The mixture was stirred at rt overnight (˜17 h). The reaction was cooled in an ice bath. Water (10 mL) was added, followed by solid KOH until pH>11. The mixture was extracted with DCM. The combined extracts were dried (MgSO4) and concentrated to afford the title compound, which was used without further purification. LC-MS: calculated for C8H9BrFN 218.07, observed m/e 219.99 (M+H)+ (Rt 0.96 min).

Provenance & Evidence