1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=0°C; 1 h; Inert atmosphere;

1: AlCl3, aluminium chloride / dichloromethane / 0 - 20 °C 2: caesium carbonate / acetonitrile / 5 h / |Reflux 3: nonafluoro-n-butanesulfonyl fluoride; N-ethyl-N,N-diisopropylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 48 h / 20 °C 4: triethylsilane; palladium dichloride / ethanol / 20 - 98 °C / |Inert atmosphere 5: lithium borohydride / tetrahydrofuran; ethanol / 0 - 20 °C 6: sodium hydroxide / methanol / 20 - 120 °C / |Sealed tube View Scheme

1: 94 percent / Ph3P, CBr4 / CH2Cl2 / 1 h 2: 1.) Mg / 1.) THF, 2.) THF, RT, 20 h 3: 18 h / Heating 4: 1.) NaBH4, 2.) 3 N HCl / 1.) MeOH, 15 min, 2.) acetone, RT, 19 h 5: BF3*Et2O / CH2Cl2 / 0.25 h View Scheme

1: 94 percent / Ph3P, CBr4 / CH2Cl2 / 1 h 2: 1.) Mg / 1.) THF, 2.) THF, RT, 20 h View Scheme

thionyl chloride

oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-55°C; Oxidation; Swern oxidation; 0.25 h;