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

Reaction equation

[F:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:3]=1N.[BH3-][C:11]#[N:12].[Na+].O.[OH-].[K+].[CH3:17]C(O)=O>>[Br:9][C:7]1[CH:6]=[CH:5][C:3]([N:12]([CH3:11])[CH3:17])=[C:2]([F:1])[CH:8]=1

Participants

Reactant 5

HCID 176Acetic Acid

HCID 962Water

HCID 14797Potassium Hydroxide

HCID 1230504-Bromo-2-fluoroaniline

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 404253644-bromo-2-fluoro-N,N-dimethylaniline

Procedure

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).