oxalyl dichloride; triethylamine in dimethyl sulfoxide 1.) -78 deg C, 30 min; 2.) RT, 30 min;

1: 95 percent / CBr4, PPh3 / dimethylformamide / 0 °C 2: 77 percent / acetonitrile / Heating 3: 1.) n-BuLi, LiBr, KOCMe3, 2.) HCl, 3.) LiOH / 1.) THF, -78 deg C, 2.) THF, room temperature, 10 h, 3.) MeOH, H2O, 10 h 4: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, DMAP, 2.) TiCl4 / 1.) THF, toluene, reflux, 6 h, 2.) CH2Cl2, 0 deg C, 2 h View Scheme

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 °C / Inert atmosphere 2.2: 1 h / Inert atmosphere 3.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 5.1: triphenylphosphine; diethylazodicarboxylate / diethyl ether; benzene / 14 h / 20 °C 6.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 7.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / toluene / 23 h / 80 °C / Inert atmosphere 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 9.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 10 °C View Scheme