sodium iodide in N,N-dimethyl-formamide T=60°C; 1 h;

1H-imidazole; iodine; triphenylphosphine in dichloromethane T=20°C; 5 h;

sodium iodide in acetone 1) 1 h, 25 deg C, 2) 3 h, reflux;

1: p-TsOH*H2O / methanol / 4 h / Heating 2: pyridine / 12 h / 0 - 5 °C 3: 75 percent / NaI / acetone / 6 h / Heating View Scheme

sodium iodide in acetone Finkelstein reaction; Reflux;

1: diluted methanol; sodium azide / 90 °C 2: PtO2; methanol / 2206.5 Torr / Hydrogenation View Scheme

1: 1.) LDA, 2.) N,N'-dimethylpropyleneurea / 1.) THF, -78 deg C, 50 min, 2.) -78 deg C, 5 min; -42 deg C, 3 h; -42 deg C to room temperature 2: 66 percent / TFA / CH2Cl2 / 1.) 0 deg C, 2.5 h, 2.) room temperature, 2.5 h 3: 99 percent / oxalyl chloride, DMF / CH2Cl2 / 2 h / Ambient temperature 4: 1.) n-BuLi / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2.5 h; -78 deg C to room temperature View Scheme

1: 81 percent / 1.) BuLi / 1.) hexane, THF, -70 degC to 0 degC, 3 h, 2a.) THF, -78 degC, 1 h, 2b.) room temp., 12 h 2: 78 percent / HgCl2, HgO / methanol; H2O / 3 h / Heating 3: 87 percent / 1.) BuLi / 1.) hexane, THF, -70 degC to room temp., 3 h, 2.a) THF, -70 degC, 1 h, 2b.) room temp., overnight 4: 93 percent / 1.) BuLi / 1.) hexane, THF, HMPA, -78 degC to room temp. in 3 h, 2a.) -78 degC, 1 h, 2b.) room temp. overnight 5: 82 percent / HgCl2, HgO / methanol; H2O / a.) room temp., 5 h, b.) 50 degC, 1 h View Scheme

1: 1.) LDA, 2.) N,N'-dimethylpropyleneurea / 1.) THF, -78 deg C, 50 min, 2.) -78 deg C, 5 min; -42 deg C, 3 h; -42 deg C to room temperature 2: 66 percent / TFA / CH2Cl2 / 1.) 0 deg C, 2.5 h, 2.) room temperature, 2.5 h View Scheme

1: 81 percent / 1.) BuLi / 1.) hexane, THF, -70 degC to 0 degC, 3 h, 2a.) THF, -78 degC, 1 h, 2b.) room temp., 12 h 2: 78 percent / HgCl2, HgO / methanol; H2O / 3 h / Heating 4: CaCO3 / CH2Cl2 / 0.25 h / 150 - 170 °C View Scheme