hydrogen; palladium on activated charcoal in acetic acid P=760 Torr; 5 h; Ambient temperature;

1: 71 percent / Br2 2: 82 percent / aniline, 47percent HBr / H2O / 4 h / 100 °C 3: chlorotrimethylsilane / 3 h / Heating 4: SnCl4 / 1,2-dichloro-ethane / 18 h / Ambient temperature 5: 80 percent / H2 / 5percent Pd/C / acetic acid / 5 h / 760 Torr / Ambient temperature View Scheme

1: chlorotrimethylsilane / 3 h / Heating 2: SnCl4 / 1,2-dichloro-ethane / 18 h / Ambient temperature 3: 80 percent / H2 / 5percent Pd/C / acetic acid / 5 h / 760 Torr / Ambient temperature View Scheme

1: 82 percent / aniline, 47percent HBr / H2O / 4 h / 100 °C 2: chlorotrimethylsilane / 3 h / Heating 3: SnCl4 / 1,2-dichloro-ethane / 18 h / Ambient temperature 4: 80 percent / H2 / 5percent Pd/C / acetic acid / 5 h / 760 Torr / Ambient temperature View Scheme

1: SnCl4 / 1,2-dichloro-ethane / 18 h / Ambient temperature 2: 80 percent / H2 / 5percent Pd/C / acetic acid / 5 h / 760 Torr / Ambient temperature View Scheme