hydrogenchloride in water; acetic acid T=20°C;

1: thionyl chloride / CH2Cl2 / 1 h / Heating 2: triethylamine / CH2Cl2 / 1 h / Ambient temperature 3: glacial acetic acid, conc. HCl / 17 h / Ambient temperature View Scheme

1: triethylamine / CH2Cl2 / 1 h / Ambient temperature 2: glacial acetic acid, conc. HCl / 17 h / Ambient temperature View Scheme

1.1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 2.1: borane-THF / tetrahydrofuran / 0 °C / Reflux 3.1: acetic acid / dichloromethane / 0.5 h / 0 - 20 °C 3.2: 20 °C 4.1: hydrogen bromide; tetra-(n-butyl)ammonium iodide / acetic acid / 100 °C 5.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.5 h 5.2: 120 °C View Scheme

1: palladium 10 on activated carbon; hydrogen / acetic acid / 8 h / 3102.97 Torr 2: borane-THF / tetrahydrofuran / 0 °C / Reflux View Scheme

palladium 10 on activated carbon; hydrogen in acetic acid P=3102.97 Torr; 8 h;