1: 87 percent / AsCl3 / diethyl ether; tetrahydrofuran / -78 deg C to RT 2: 63 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 1) -78 deg C to RT, 2) reflux, 15 min 3: 85 percent / 2 h / 150 °C View Scheme

1: 98 percent / tetrahydrofuran / 2 h 2: 16.7 g / H2O2 / H2O; CHCl3 / 1 h 3: 71 percent / Br2 / CHCl3 / 1.5 h / Ambient temperature; other solvent 4: 100 percent / HSiCl3, pyridine / benzene / Heating 5: 61 percent / NaOMe / methanol; benzene / 96 h / Heating View Scheme