potassium hydride in 1-methyl-pyrrolidin-2-one T=20°C; 3 h; Inert atmosphere;

palladium 10 on activated carbon; hydrogen; acetic acid in ethyl acetate T=20°C; P=7500.75 Torr; 24 h; Autoclave;

1: hydrogenchloride; iron / ethanol; water / 1.5 h / 0 - 20 °C / Inert atmosphere 2: N-bromosuccinmide / 1,4-dioxane / 14 h / 23 °C / Inert atmosphere 3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 5 h / 50 °C / Inert atmosphere 4: potassium hydride / 1-methyl-pyrrolidin-2-one / 3 h / 20 °C / Inert atmosphere View Scheme

1: N-bromosuccinmide / 1,4-dioxane / 14 h / 23 °C / Inert atmosphere 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 5 h / 50 °C / Inert atmosphere 3: potassium hydride / 1-methyl-pyrrolidin-2-one / 3 h / 20 °C / Inert atmosphere View Scheme