aluminium trichloride in chlorobenzene 4 h; Heating;

1.1: 91 percent / LiAlH4 / diethyl ether / 2 h / 20 °C 2.1: 100 percent / PBr3 / hexane; CH2Cl2 / 6 h / 20 °C 3.1: n-BuLi; diisopropylamine / tetrahydrofuran; cyclohexane / 1 h / -78 °C 3.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / 2 h / -78 °C 4.1: 83 percent / AlCl3 / chlorobenzene / 4 h / Heating View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; cyclohexane / 1 h / -78 °C 1.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / 2 h / -78 °C 2.1: 83 percent / AlCl3 / chlorobenzene / 4 h / Heating View Scheme

1.1: 100 percent / PBr3 / hexane; CH2Cl2 / 6 h / 20 °C 2.1: n-BuLi; diisopropylamine / tetrahydrofuran; cyclohexane / 1 h / -78 °C 2.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; cyclohexane / 2 h / -78 °C 3.1: 83 percent / AlCl3 / chlorobenzene / 4 h / Heating View Scheme

1.1: potassium carbonate / acetone / 24 h / 70 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / |Inert atmosphere 3.1: phosphorus tribromide / dichloromethane / 6 h / 20 °C / |Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran / 0.33 h / -78 °C / |Inert atmosphere 4.2: 2 h / -78 °C / |Inert atmosphere 5.1: AlCl3, aluminium chloride / chlorobenzene / 4 h / |Reflux View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 2 h / 20 °C 2: Fremy’s salt; sodium acetate / methanol; N,N-dimethyl-formamide; water / 14 h / 20 °C View Scheme