copper(l) iodide; N-acetyl-glycine; potassium iodide; sodium hydroxide in tert-butyl alcohol T=100°C; 24 h;

1: 90 percent / aq. K2CO3; conc. H2O2 / ethanol / 14 h / 20 °C 2: 83 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H2O / 24 h / 20 °C View Scheme

1.1: dimethylsulfide borane complex / tetrahydrofuran / 19 h / 0 °C / |Reflux 2.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: polyphosphoric acid / 1 h / 150 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 19 h / 0 °C / |Reflux 4.2: 18 h / |Reflux View Scheme

1: 2-(2'-bromophenyl)-acetonitrile With potassium tert-butylate in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0°C; 0.166667 h; Inert atmosphere; 2: methyl iodide in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0 - 10°C; 1.16667 h; Inert atmosphere;

1: With sodium hexamethyldisilazane in tetrahydrofuran T=65°C; 1 h; 2: With hydrogenchloride; water in tetrahydrofuran

1.1: sodium hydroxide; tert-butyl alcohol / 13 h / 100 °C / |Sealed tube 2.1: sodium hydride / hexane; tetrahydrofuran / 1 h / 20 °C / |Schlenk technique 2.2: 70 °C / |Schlenk technique 3.1: 1,2-diamino-benzene; copper(I) oxide; sodium t-butanolate / tert-butyl alcohol / 48 h / 100 °C / |Sealed tube View Scheme