1: anhydrous iron chloride; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 3: phosphorus tribromide / chloroform / 4 h / 20 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 20 °C 5: acetic acid / methanol / 3 h / 45 °C 6: potassium hydroxide / 1,4-dioxane; methanol / 3 h 7: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Reflux 8: tin(IV) chloride / dichloromethane / 6 h / Reflux 9: sodium tetrahydroborate / ethanol / 6 h / 0 - 20 °C 10: triethylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / Reflux 11: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / Reflux View Scheme

1: Cu / quinoline / 210 - 220 °C 2: cyclohexene, EtOH / Pd-C View Scheme