4-Bromo-2,6-difluoroaniline → 4-Amino-3,5-difluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of CuCN (135 mg, 1.51 mmol) and 4-bromo-2,6-difluorobenzenamine (200 mg, 0.96 mmol) in DMF (4 mL) was sealed in a microwave vial and degassed with Ar. The mixture was heated in microwave at 220° C. for 17.5 min. Ammonium hydroxide (10 mL) and water (10 mL) were added to the mixture and it was extracted with EtOAc (2×20 mL). The organics were combined, washed with sat. NaHCO3 and brine, dried (Na2SO4) and concentrated. Purification by flash chromatography yielded 116 mg of Intermediate 383.1 as a white solid. LCMS 155.3 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 4.27 (bs, 2H) 7.12 (dd, J=5.87, 2.20 Hz, 2H).

Provenance & Evidence