hydrogen bromide; acetic acid T=100°C; 0.25 h;

1: 74 percent / NaOAc, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 23 deg C, 64 h 2: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) THF, -65 deg C 3: 81 percent / 48percent HBr, HOAc / 0.25 h / 100 °C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) THF, -65 deg C 2: 81 percent / 48percent HBr, HOAc / 0.25 h / 100 °C View Scheme

1: 75 percent / methanol / 68 h / Heating 2: 74 percent / anhydrous sodium acetate, Br2 / acetic acid / 1.) 80 deg C, 6 h, 2.) 23 deg C, 64 h; 3: 1.) n-butyllithium / 1.) ether, hexane, -70 deg C, 15 min, 2.) -60 deg C; 4: 80 percent / 48percent HBr / acetic acid / 95 - 100 °C View Scheme

hydrogen; W-2 Raney nickel in tetrahydrofuran; ethanol