toluene-4-sulfonic acid in benzene Heatingazeotropic removal of water;

1: PBr3 / diethyl ether / 15 h / 0 °C 2: 79 percent / NaH, n-BuLi / tetrahydrofuran / 0 °C 3: p-TsOH / benzene / Heating View Scheme

1: 79 percent / NaH, n-BuLi / tetrahydrofuran / 0 °C 2: p-TsOH / benzene / Heating View Scheme

1: 1) NaH (60percent in oil), 2) n-BuLi / 1) THF, 0 deg C, 30 min, 2) THF, hexane, 0 deg C, 10 min, 3) THF, hexane, 0 deg C, 30 min then RT, 1 h 2: 82 percent / p-TsOH / benzene / Heating; azeotropic removal of water View Scheme

1: LiAlH4 / diethyl ether 2: CBr4, PPh3 / benzene / 0.5 h / Heating View Scheme