1: NH3 (gaseous) / benzene / 0.5 h 2: 60.6 percent / LiBH4 / tetrahydrofuran / 2 h / Heating 3: 34.5 percent / Ba(OH)2, Br2 / H2O / 5 deg C to RT, 2 h; 65-70 deg C, 1 h View Scheme

1: NH3 (gaseous) / benzene / 0.5 h 2: 60.6 percent / LiBH4 / tetrahydrofuran / 2 h / Heating 3: 34.5 percent / Ba(OH)2, Br2 / H2O / 5 deg C to RT, 2 h; 65-70 deg C, 1 h 4: 42 percent / dimethylformamide / Ambient temperature View Scheme