boron trichloride in dichloromethane T=20°C;

nitric acid in chloroform T=-20°C; 0.166667 h;

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 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 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 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 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