pyridine; phosphorus tribromide in benzene T=55°C; 6 h;

1: 74 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h; 2.) room temperature, 14 h 2: 74.5 percent / PBr3, pyridine / benzene / 6 h / 55 °C View Scheme

1: 72 percent / AlCl3 / CH2Cl2 / 1.) 0 deg C; 2.) ambient temp. 4 h; 3.) reflux, 2.5 h 2: 38.5 percent / NaOCl / H2O / 4.5 h / Heating 3: 74 percent / LiAlH4 / diethyl ether / 1.) reflux, 3 h; 2.) room temperature, 14 h 4: 74.5 percent / PBr3, pyridine / benzene / 6 h / 55 °C View Scheme