1: 90 percent / concd. HCl / ethanol 2: 1.) aq. HCl, sodium nitrite, 2.) 48percent aq. HBF4 / 1.) 0 deg C, 5 min, 2.) 0 deg C, 30 min 3: 13 percent / 48percent aq. HBF4 / 1 h / Irradiation View Scheme

sulfuric acid; potassium iodide; sodium nitrite 1.) H2O, 0 deg C, 45 min 2.) H2O; Yield given. Multistep reaction;

1: 90 percent / concd. HCl / ethanol 2: 1.) aq. HCl, sodium nitrite, 2.) aq. KI / 1.) 0 deg C, 10 min 3: 88 percent / Mg/CH3I / tetrahydrofuran / 21 h / Heating View Scheme