1: pyridine / 4 h / Ambient temperature 2: 2.) FeCl3, conc HCl / 1.) DMF, 152 deg C, 7 h; 2.) DMF, water, 65 - 70 deg C, 20 min 3: 34 percent / NaOH / aq. ethanol / 1 h / Heating View Scheme

1: Br2 / dioxane / 4 h / Ambient temperature 2: pyridine / 4 h / Ambient temperature 3: 2.) FeCl3, conc HCl / 1.) DMF, 152 deg C, 7 h; 2.) DMF, water, 65 - 70 deg C, 20 min 4: 34 percent / NaOH / aq. ethanol / 1 h / Heating View Scheme

in pyridine; toluene 3 h; Heating;