sodium hydroxide in ethanol 1 h; Heating;

1: 85 percent / hexamethylphosphoric acid triamide / 0.5 h / 0 °C 2: 92 percent / diethyl ether / 12 h / 0 - 5 °C 3: 1.) (n-Bu)3SnH, azobisbutyronitrile, 2.) iodine monochloride / 1.) toluene, reflux, 6 h, 2.) CCl4 4: 67 percent / 1 N aq. NaOH / ethanol / 1 h / Heating View Scheme

1: 92 percent / diethyl ether / 12 h / 0 - 5 °C 2: 1.) (n-Bu)3SnH, azobisbutyronitrile, 2.) iodine monochloride / 1.) toluene, reflux, 6 h, 2.) CCl4 3: 67 percent / 1 N aq. NaOH / ethanol / 1 h / Heating View Scheme

1: 1.) (n-Bu)3SnH, azobisbutyronitrile, 2.) iodine monochloride / 1.) toluene, reflux, 6 h, 2.) CCl4 2: 67 percent / 1 N aq. NaOH / ethanol / 1 h / Heating View Scheme