1-(2-bromo-4-fluorophenyl)-N,N-dimethylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 2-bromo-4-fluorobenzaldehyde (5 g, 24.63 mmol), dimethylamine (2 M, 49.26 mL, 98.52 mmol) and acetic acid (8.47 mL, 147.78 mmol) in DCM (50 mL), and stir for 30 min. To this mixture, add sodium triacetoxyborohydride (49.26 mmol, 10.44 g) and stir overnight at RT. Wash with saturated NaHCO3 solution (100 mL), dry with aqueous saturated sodium chloride, and then dry over sodium sulfate. Filter the organics and remove the solvent under reduced pressure to give the title compound as a brownish oil (4.56 g). GCMS m/z 232 [M]+. Wash with saturated NaHCO3 solution (100 mL) dry with aqueous saturated sodium chloride dry over sodium sulfate Filter the organics and remove the solvent under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine 2-bromo-4-fluorobenzaldehyde (5 g, 24.63 mmol), dimethylamine (2 M, 49.26 mL, 98.52 mmol) and acetic acid (8.47 mL, 147.78 mmol) in DCM (50 mL), and stir for 30 min. To this mixture, add sodium triacetoxyborohydride (49.26 mmol, 10.44 g) and stir overnight at RT. Wash with saturated NaHCO3 solution (100 mL), dry with aqueous saturated sodium chloride, and then dry over sodium sulfate. Filter the organics and remove the solvent under reduced pressure to give the title compound as a brownish oil (4.56 g). GCMS m/z 232 [M]+. Wash with saturated NaHCO3 solution (100 mL) dry with aqueous saturated sodium chloride dry over sodium sulfate Filter the organics and remove the solvent under reduced pressure