in benzene Heating;

1: K2CO3 / dimethylformamide / Ambient temperature 2: 62 percent / NBS, AIBN / CCl4 / Heating 3: 73 percent / toluene / Heating View Scheme

1: 62 percent / NBS, AIBN / CCl4 / Heating 2: 73 percent / toluene / Heating View Scheme

1: PBr3 2: 76 percent / benzene / Heating View Scheme

1: LiAlH4 / tetrahydrofuran 2: PBr3 3: 76 percent / benzene / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 - 20 °C / Inert atmosphere 2.1: copper(II) bis(trifluoromethanesulfonate); (-)-2,2′-isopropylidenebis[(4S)-4-phenyl-2-oxazoline] / dichloromethane / 3 h / 32 °C / Inert atmosphere; Molecular sieve 2.2: 1 h / 32 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 4 h / 20 °C / Inert atmosphere 4.1: p-methoxyphenyl mercaptan; potassium carbonate / dimethyl sulfoxide; acetonitrile / 5 h / 20 °C / Inert atmosphere View Scheme

n-butyllithium in tetrahydrofuran Yield given;