1: 1.) NaH / 1.) 1,2-dimethoxyethane, RT, 15 min, 2.) 1,2-dimethoxyethane, RT, 2 h 2: 70 percent / hydrazine / 5percent Pd/C / ethanol / 0.5 h / Heating 3: 95 percent / 1 h / 50 °C 4: 1.) iodine, air, 2.) conc. HCl / 1.) benzene, irradiation, 4 h, 2.) ethanol, reflux, 10 h View Scheme

1: 1.) NaH / 1.) 1,2-dimethoxyethane, RT, 15 min, 2.) 1,2-dimethoxyethane, RT, 2 h 2: 70 percent / hydrazine / 5percent Pd/C / ethanol / 0.5 h / Heating 3: 95 percent / 1 h / 50 °C 4: 1.) iodine, air, 2.) conc. HCl / 1.) benzene, irradiation, 4 h, 2.) ethanol, reflux, 10 h View Scheme

1: 70 percent / hydrazine / 5percent Pd/C / ethanol / 0.5 h / Heating 2: 95 percent / 1 h / 50 °C 3: 1.) iodine, air, 2.) conc. HCl / 1.) benzene, irradiation, 4 h, 2.) ethanol, reflux, 10 h View Scheme

1: 95 percent / 1 h / 50 °C 2: 1.) iodine, air, 2.) conc. HCl / 1.) benzene, irradiation, 4 h, 2.) ethanol, reflux, 10 h View Scheme

hydrogenchloride; air; iodine 1.) benzene, irradiation, 4 h, 2.) ethanol, reflux, 10 h; Yield given. Multistep reaction. Yields of byproduct given;