1: 61 percent / ethanol / 1.) 60 deg C, 3 h, 2.) room temp., 3 h, 3.) -20 deg C, overnight 2: sodium hydride / 1.) THF, 2 h, 2.) pentane, 2 h 3: 60 °C / 0 Torr 4: 8.9 percent / p-toluenesulfonic acid / ethanol View Scheme

1: 61 percent / ethanol / 1.) 60 deg C, 3 h, 2.) room temp., 3 h, 3.) -20 deg C, overnight 2: sodium hydride / 1.) THF, 2 h, 2.) pentane, 2 h 3: 60 °C / 0 Torr 4: 8.9 percent / p-toluenesulfonic acid / ethanol 5: bromine / benzene / Irradiation View Scheme