hydrogen bromide; 3-chloro-benzenecarboperoxoic acid in toluene T=0 - 20°C; Inert atmosphere;

1: With lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether T=75°C; 1 h; 2: With methanesulfonyl chloride; triethylamine in dichloromethane T=0°C; 1 h; 3: With lithium bromide in acetone 8.5 h; Heating; Further stages. Title compound not separated from byproducts.;

phosphorus tribromide

1: LiAlH4 / diethyl ether / 18 h / Heating 2: 10.1 g / PBr3 / 3 h / 100 °C View Scheme

1.1: 82 percent / NBS; dibenzoyl peroxide / CCl4 / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: tetrahydrofuran; hexane / 18 h / -78 °C 3.1: aq. HCl / 100 °C 4.1: LiAlH4 / diethyl ether / 18 h / Heating 5.1: 10.1 g / PBr3 / 3 h / 100 °C View Scheme

1: aq. HCl / 100 °C 2: LiAlH4 / diethyl ether / 18 h / Heating 3: 10.1 g / PBr3 / 3 h / 100 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 1.2: tetrahydrofuran; hexane / 18 h / -78 °C 2.1: aq. HCl / 100 °C 3.1: LiAlH4 / diethyl ether / 18 h / Heating 4.1: 10.1 g / PBr3 / 3 h / 100 °C View Scheme

(i) aq. EtOH, (ii) H2SO4, AcOH; Multistep reaction;

1.1: magnesium turnings; 1,2-dibromoethane / tetrahydrofuran / 24 h / Heating 1.2: 45 percent / LiAlH4 / tetrahydrofuran / 20 h / Heating 2.1: Cl2 / CCl4 / 0.07 h / 0 °C View Scheme

1.1: magnesium; 1,2-dibromoethane / tetrahydrofuran / 14 h / Heating 1.2: 43 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating 2.1: Cl2 / CCl4 / 0.07 h / 0 °C 3.1: potassium hydride / tetrahydrofuran / 1 h / Heating 3.2: 33 percent / tetrahydrofuran / 4 h / Heating 4.1: 90 percent / DIBAL-H / heptane / 20 h / 100 °C View Scheme