1.1: bromine / 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 1 h / 0 °C 2.2: 0 °C 3.1: n-butyllithium / diethyl ether / 0.17 h / -78 °C / |Inert atmosphere 3.2: 0.17 h / |Inert atmosphere 4.1: sodium tetrahydroborate / diethylene glycol dimethyl ether / 1.5 h / 20 °C 5.1: phosphorus tribromide / benzene / 45 h / |Reflux View Scheme

1: sodium tetrahydroborate / diethylene glycol dimethyl ether / 1.5 h / 20 °C 2: phosphorus tribromide / benzene / 45 h / |Reflux View Scheme

1.1: n-butyllithium / diethyl ether; hexane / 1 h / 0 °C 1.2: 0 °C 2.1: n-butyllithium / diethyl ether / 0.17 h / -78 °C / |Inert atmosphere 2.2: 0.17 h / |Inert atmosphere 3.1: sodium tetrahydroborate / diethylene glycol dimethyl ether / 1.5 h / 20 °C 4.1: phosphorus tribromide / benzene / 45 h / |Reflux View Scheme

1.1: n-butyllithium / diethyl ether / 0.17 h / -78 °C / |Inert atmosphere 1.2: 0.17 h / |Inert atmosphere 2.1: sodium tetrahydroborate / diethylene glycol dimethyl ether / 1.5 h / 20 °C 3.1: phosphorus tribromide / benzene / 45 h / |Reflux View Scheme