1: 1.) Mg, CCl4 / 1.) EtOH, Et2O, 3 h, 2.) EtOH, Et2O, THF, reflux, 16 h 2: 65 percent / H2SO4 / acetic acid; H2O / 3.5 h / Heating 3: 89 percent / SnCl2*2H2O, conc. aq. HCl / 0.12 h / 95 °C 4: 1.) NaNO2, 3percent aq. H2SO4, 2.) NaI / 1.) 0-5 deg C, 30 min, 2.) water, CH2Cl2, 5 deg C, 35 min View Scheme

1: 65 percent / H2SO4 / acetic acid; H2O / 3.5 h / Heating 2: 89 percent / SnCl2*2H2O, conc. aq. HCl / 0.12 h / 95 °C 3: 1.) NaNO2, 3percent aq. H2SO4, 2.) NaI / 1.) 0-5 deg C, 30 min, 2.) water, CH2Cl2, 5 deg C, 35 min View Scheme

sulfuric acid; sodium iodide; sodium nitrite 1.) 0-5 deg C, 30 min, 2.) water, CH2Cl2, 5 deg C, 35 min; Yield given. Multistep reaction;

1: 89 percent / SnCl2*2H2O, conc. aq. HCl / 0.12 h / 95 °C 2: 1.) NaNO2, 3percent aq. H2SO4, 2.) NaI / 1.) 0-5 deg C, 30 min, 2.) water, CH2Cl2, 5 deg C, 35 min View Scheme