1: 86 percent / PPh3; CBr4 / CH2Cl2 / 14 h / 20 °C 2: 98 percent / BBr3 / CH2Cl2 / 6.75 h / -78 - 20 °C 3: 37.5 percent / MgSO4; BF3*Et2O / CH2Cl2 / 2.5 h / 0 °C 4: 47 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 2: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 4: H2 / 10percent Pd/C View Scheme

1: 86 percent / PPh3; CBr4 / CH2Cl2 / 14 h / 20 °C 2: 98 percent / BBr3 / CH2Cl2 / 6.75 h / -78 - 20 °C View Scheme