hydrogenchloride; iron in methanol; water 2 h; Reflux;

1: hydrogenchloride / water / 110 °C / Inert atmosphere 2: water; iron; acetic acid / 1.25 h / 20 °C / Inert atmosphere; Cooling View Scheme

1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 2: hydrogenchloride / water / 110 °C / Inert atmosphere 3: water; iron; acetic acid / 1.25 h / 20 °C / Inert atmosphere; Cooling View Scheme

1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 2.2: 40 - 60 °C 2.3: 0 - 20 °C 3.1: triethylamine / 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl; palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr View Scheme

1: With potassium acetate; acetic anhydride in chloroform T=20°C; 5 h; Reflux; 2: With 18-crown-6 ether; isopentyl nitrite in chloroform T=20°C; 26 h; Reflux; 3: With potassium carbonate in methanol; water T=0°C; 2 h;

1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 2.2: 40 - 60 °C 2.3: 0 - 20 °C 3.1: triethylamine / 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl; palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr 4.1: sodium hydroxide; water / methanol / 0 - 20 °C 4.2: pH 5 - 6 View Scheme

1.1: triethylamine / dichloromethane / 18 h 1.2: 1 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 3 h / Reflux 3.1: potassium carbonate; methanol / 1 h / Reflux 4.1: N-ethyl-N,N-diisopropylamine / bis(benzonitrile)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 4 h / 135 °C / 11251.1 Torr View Scheme