1: 98 percent / thionyl chloride, 2,6-lutidine / toluene / 2 h / 35 °C 2: 52 percent / K2CO3 / ethanol / 80 °C 3: 59 percent / Bu3SnH, AIBN / benzene / 12 h / 100 °C View Scheme

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 3 h / 20 °C / |Cooling with ice 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1 h / 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 20 °C / |Cooling with ice 3.2: 2 h / 20 °C / |Cooling with ice 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.67 h / 50 °C / |Cooling with ice 4.2: 4 h / 20 °C 5.1: 20 palladium(II) hydroxide on carbon; hydrogen / methanol / 4 h / 20 °C / |Inert atmosphere View Scheme