quinoline; nitrobenzene

sulfuric acid; hydroquinone in benzene Heating;

1: bromine trichloride, 1 percent pyridine / neat (no solvent) 2: 87 percent / bromine trifluoride, 1 mol percent tin tetrachloride / 1,1,2-trichloro-1,2,2-trifluoro-ethane / 20 - 30 °C 3: 90 percent / triethylamine / CH2Cl2 / 20 - 40 °C View Scheme