hydrogenchloride; hydrogen; palladium 10 on activated carbon in water; ethyl acetate P=3345.86 Torr;

1.1: potassium tert-butylate / toluene / 78 °C / Inert atmosphere 1.2: 78 °C / Inert atmosphere 1.3: 78 °C / Inert atmosphere 2.1: zinc(II) chloride / toluene; tetrahydrofuran / 6 h / Reflux; Inert atmosphere 3.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere 4.1: nitric acid / chloroform / 1 h / 0 - 20 °C 5.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C 5.2: 20 °C 6.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h 7.1: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 8.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme

1.1: zinc(II) chloride / toluene; tetrahydrofuran / 6 h / Reflux; Inert atmosphere 2.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere 3.1: nitric acid / chloroform / 1 h / 0 - 20 °C 4.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C 4.2: 20 °C 5.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h 6.1: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 7.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme

1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h 2: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 3: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme

1.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C 1.2: 20 °C 2.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h 3.1: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 4.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme

1: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 2: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme

1.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere 2.1: nitric acid / chloroform / 1 h / 0 - 20 °C 3.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C 3.2: 20 °C 4.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h 5.1: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 6.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme

1.1: nitric acid / chloroform / 1 h / 0 - 20 °C 2.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C 2.2: 20 °C 3.1: 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h 4.1: sodium bromide; KF*2H2O / tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel 5.1: ammonium chloride; iron / ethanol; water; tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme