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

1: 79 percent / 33percent HBr/HOAc / 18 h / 80 °C 2: 97 percent / LiAlH4 / tetrahydrofuran / 20 h / Ambient temperature 3: 1.) n-butyllithium / 1.) petroleum ether, hexane, reflux, 20 h, 2.) petroleum ether, haxane, reflux, 22 h View Scheme

1: 96 percent / H2NNH2; AcOH 2: n-BuLi / tetrahydrofuran / -78 °C View Scheme

1: 96 percent / H2NNH2; AcOH View Scheme

1: 97 percent / oxalyl chloride; dimethylsulfoxide / CH2Cl2 / 1.3 h / -60 °C 2: 96 percent / hydrazine monohydrate / acetic acid / 2.5 h 3: 67 percent / tert-butyllithium; diiodoethane / tetrahydrofuran View Scheme