1: CH2Cl2 / 14 h / Ambient temperature 2: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 3: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 30 min, 2.) THF/hexane, -15 deg C, 5 h View Scheme

1: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 2: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 30 min, 2.) THF/hexane, -15 deg C, 5 h View Scheme

1: thionyl chloride / 1 h / 100 °C 2: CH2Cl2 / 14 h / Ambient temperature 3: 70 percent / thionyl chloride / benzene; CH2Cl2 / 1.) reflux, 2.) room temperature, 2.5 h 4: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 30 min, 2.) THF/hexane, -15 deg C, 5 h View Scheme

n-butyllithium 1.) THF, -78 deg C, 2.) allowed to warm to ambient temperature; Yield given. Multistep reaction;