pyridine; phosphorus tribromide in diethyl ether a.) standing overnight b.) 2h reflux;

1: 50 percent / NH3(liq), Li / Fe(NO3)3 / tetrahydrofuran / 3 h 2: 95 percent / Lindlar's catalyst / hexane 3: 90 percent / PBr3,Py / diethyl ether / a.) standing overnight b.) 2h reflux View Scheme

1: 70 percent / benzene / 16 h / Heating 2: 78 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 140 - 145 °C 3: 90 percent / LiAlH4 / diethyl ether / a.) reflux while adding reagent b.) room temperature overnight c.) 30 min reflux View Scheme

1: 70 percent / benzene / 16 h / Heating 2: 78 percent / NaCl, H2O / dimethylsulfoxide / 8 h / 140 - 145 °C 3: 90 percent / LiAlH4 / diethyl ether / a.) reflux while adding reagent b.) room temperature overnight c.) 30 min reflux 4: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h View Scheme

1: 50 percent / Mg, LiCl, CuCl2 / tetrahydrofuran 2: 82 percent / PTS / methanol / 3 h / Heating 3: 70 percent / pyridine / 24 h / Ambient temperature View Scheme