hydrogen; palladium on activated charcoal in ethanol; acetic acid

in ethanol T=50°C; 2 h;

1: 90 percent / Ac2O / 48 h / Ambient temperature 2: 80 percent / Br2 / CHCl3 / 0.5 h / Heating 3: 76 percent / ethanol / 2 h / 50 °C View Scheme

1: 80 percent / Br2 / CHCl3 / 0.5 h / Heating 2: 76 percent / ethanol / 2 h / 50 °C View Scheme

1: AlCl3, aluminium chloride; bromine / diethyl ether / 1 h / 0 - 20 °C 2: ethanol / 0.5 h / 80 °C 3: palladium 10 on activated carbon; sodium tetrahydroborate / dichloromethane; methanol / 5 h / 0 °C View Scheme