1: bromine / dichloromethane / 2.5 h / 0 °C 2: dichloromethane; toluene / 16 h / |Reflux 3: sodium hydroxide / methanol; water / 3 h / 40 °C 4: triethylamine; hydrogen / methanol / 2 h / 70 °C / 6080.41 - 7600.51 Torr / |Autoclave; |Inert atmosphere 5: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 1 h / 70 °C 6: 10 h / 95 °C 7: N,N-dimethyl-formamide / 20 h / 120 °C / |Inert atmosphere 8: hydrogen; palladium on activated charcoal / methanol / 3 h / 20 °C / 11251.1 Torr View Scheme

1.1: bromine; acetic acid / 0.67 h / 20 °C 2.1: N,N-dimethyl-formamide / 150 °C / Inert atmosphere 2.2: 0.25 h / 70 °C 3.1: ammonium acetate / 4.5 h / 125 °C 3.2: 0.5 h / 20 °C 4.1: hydrogenchloride; water; iron; anhydrous iron chloride / 2.5 h / 60 - 90 °C 5.1: tetrahydrofuran / 0.17 h / 20 °C 5.2: 24 h / 20 °C 6.1: sodium carbonate / water / 0.5 h / 20 °C 7.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 21.5 h / 110 °C / Sealed tube 8.1: hydrogen / 5 palladium on charcoal / ethanol / 19 h / 50 °C / 9000.9 Torr 9.1: sodium hydroxide; dihydrogen peroxide / water; dimethyl sulfoxide / 20.17 h / 20 °C / Cooling with ice; Inert atmosphere 10.1: trimethylsilyl iodide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere View Scheme