1: 81 percent / Fe, HOAc / ethanol / 6 h / Heating View Scheme

1: 1.) conc. H2SO4, 2.) sodium nitrite / ethanol / 1.) EtOH, reflux, 2.) reflux, 1 h 2: 81 percent / Fe, HOAc / ethanol / 6 h / Heating View Scheme

1: 35 percent / iodine monochloride, glacial acetic acid / 3 h / 120 °C 2: 1.) conc. H2SO4, 2.) sodium nitrite / ethanol / 1.) EtOH, reflux, 2.) reflux, 1 h 3: 81 percent / Fe, HOAc / ethanol / 6 h / Heating View Scheme

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Multistep reaction. Yields of byproduct given;