palladium on activated charcoal; hydrogen; acetic acid in methanol

1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 5 h / 100 °C / |Sealed tube 2: hydrogen; palladium 10 on activated carbon / ethanol; ethyl acetate / 3 h / 20 °C / 2068.65 Torr / |Inert atmosphere View Scheme

1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 5 h / 100 °C / |Sealed tube 2: hydrogen; palladium 10 on activated carbon / ethanol; ethyl acetate / 3 h / 20 °C / 2068.65 Torr / |Inert atmosphere View Scheme

1.1: N-bromosuccinmide / dichloromethane / 10 h / 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / ethanol; water; toluene / 3 h / 80 °C 3.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 0.25 h / 25 °C 3.2: 25 °C 4.1: ethanol / dichloromethane / 25 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.67 h / 0 - 20 °C View Scheme