hydrogen bromide in benzene 1.) room temperature, 12 h; 2.) 75 deg C, 3 h; 3.) room temperature, 6 h;

1: 90 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h; 2.) room temperature, 14 h 2: 42 percent / PBr3, pyridine / benzene / 6 h / 55 °C View Scheme