Ethyl Acetate → 3-Bromo-5-(dimethylamino)benzonitrile

Participants

Reaction Steps

To a stirring suspension of 210 mg (10.6 mmol) of 3-amino-5-bromobenzonitrile in 11 mL of CH3CN and 11 mL of 37% formaldehyde in H2O was added 222 mg (3.53 mmol) of NaCNBH3 followed by about 7 drops of acetic acid to a pH=7. After 1 h 40 min., an additional amount of acetic acid (10 drops) was added. After 15 h, 40 mL of EtOAc and 40 mL of sat. NaHCO3 was added, and the layers were separated. The organic layer was washed with 25 mL of sat. NaHCO3 and 25 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided 67.4 mg of 3-bromo-5-(dimethylamino)benzonitrile as a yellow solid in 28% yield.

Provenance & Evidence