oxygen; copper dichloride in tetrahydrofuran T=100°C; P=760.051 Torr; 12 h;

ammonium cerium(IV) nitrate in water; acetonitrile T=20°C; 15 h;

CaH2 in N,N-dimethyl-formamide T=60°C; 2 h;

1,4-diaza-bicyclo[2.2.2]octane in chloroform Friedel-Crafts acylation; 22 h; Heating;

air in chloroform Cyclization; 18 h; Heating;

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 20 °C / |Inert atmosphere 2: potassium carbonate / methanol / 2.5 h / 20 °C 3: hydrogenchloride; water / methanol / 12 h / 50 °C 4: copper(l) iodide; 2,2,2-trimethylacetic acid; oxygen / dimethyl sulfoxide / 23 h / 130 °C View Scheme

potassium hydroxide in ethanol

1: (COCl)2 / Ambient temperature 2: i-Pr2NEt / tetrahydrofuran / 1 h / 35 °C 3: Br2 / 0.03 h View Scheme

1: 5-Fluoro-1H-indol-2,3-dione With sodium hydride in N,N-dimethyl-formamide; mineral oil Cooling; 2: MeX, X = halide in N,N-dimethyl-formamide; mineral oil

bromine 0.0333333 h; Yield given;