thionyl chloride

1: 1.) n-BuLi / 1.) THF, 20 deg C, 2.) Et2O 2: SOCl2, DMF / toluene / 1 h / 60 °C View Scheme

1: aqueous NaClO 2: SOCl2 View Scheme

1: 1.) TiCl4, 2.) Et3N / 1.) CHCl3, reflux, 1 h, 2.) benzene, reflux, 2 h 2: 19 percent / methanol / 15 h / Irradiation 3: 95 percent / Pb(OAc)4 / benzene / 2 h / 50 °C View Scheme