1: AlCl3 / 4 h / 45 - 50 °C 2: 80 percent NH2NH2, KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 3: 24.1 percent / AlCl3 / CH2Cl2 / 3 h / 0 °C 4: 88.9 percent / Br2, NaOH / dioxane / 5 h View Scheme

1: AlCl3 / 4 h / 45 - 50 °C 2: 80 percent NH2NH2, KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating 3: 24.1 percent / AlCl3 / CH2Cl2 / 3 h / 0 °C 4: 88.9 percent / Br2, NaOH / dioxane / 5 h 5: 1) SOCl2; 2) 25 percent aq. NH3 / 1) DMF, reflux, 2.5 h; 2) DMF, dioxane 6: 32.5 g / SOCl2 / dimethylformamide / 3 h / 80 °C View Scheme