hydrogen bromide; acetic acid T=80°C; 18 h;

1: 49 percent / HCl(gas) / 48 h / Ambient temperature 2: 90 percent / LiAlH4 / diethyl ether / 48 h / Ambient temperature 3: 79 percent / 33percent HBr/HOAc / 18 h / 80 °C View Scheme

1: 1.) aq. HCl, NaNO2, 2.) Cu(I) / 1.) 5 deg C, 2.) from 10 deg C to reflux 2: 49 percent / HCl(gas) / 48 h / Ambient temperature 3: 90 percent / LiAlH4 / diethyl ether / 48 h / Ambient temperature 4: 79 percent / 33percent HBr/HOAc / 18 h / 80 °C View Scheme

1: copper-powder 2: LiAlH4; diethyl ether; 1,2-dimethoxy-ethane 3: aqueous HBr View Scheme

1: 97 percent / LiAlH4 / tetrahydrofuran / 20 h / Ambient temperature 2: 1.) n-butyllithium / 1.) petroleum ether, hexane, reflux, 20 h, 2.) petroleum ether, haxane, reflux, 22 h View Scheme