1: 68 percent / TiCl4 / CH2Cl2 / 1 h / -10 °C 2: 74 percent / NaClO2, resorcinol, NaOAc*3H2O, AcOH / H2O; dioxane / 24 h / Ambient temperature 3: 90 percent / BCl3 / various solvent(s) / 2 h / -10 °C View Scheme

1: 83 percent / aluminium chloride / benzene / 0.5 h / Heating 2: 22 percent / nitric acid, acetic acid / 4 h / 15 - 16 °C / further nitration agents 3: potassium carbonate / dimethylformamide / Ambient temperature 4: 77 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 5: 97 percent / bromine / CH2Cl2 / 0.25 h 6: 85 percent / bromine / CH2Cl2 / 19.5 h 7: 95 percent / phosphinic acid / palladized charcoal / methanol / 0.42 h / Heating 8: 1.) sodium nitrite, hydrochloric acid, 2.) phosphinic acid / 1.) dioxane, water, 0 - 5 deg C, 0.5 h, 2.) 21 h 9: 48 percent / copper bronze / 2 h / 260 °C 10: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 11: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

1: 22 percent / nitric acid, acetic acid / 4 h / 15 - 16 °C / further nitration agents 2: potassium carbonate / dimethylformamide / Ambient temperature 3: 77 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 4: 97 percent / bromine / CH2Cl2 / 0.25 h 5: 85 percent / bromine / CH2Cl2 / 19.5 h 6: 95 percent / phosphinic acid / palladized charcoal / methanol / 0.42 h / Heating 7: 1.) sodium nitrite, hydrochloric acid, 2.) phosphinic acid / 1.) dioxane, water, 0 - 5 deg C, 0.5 h, 2.) 21 h 8: 48 percent / copper bronze / 2 h / 260 °C 9: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 10: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

1: 77 percent / bromine, aluminium powder 2: 83 percent / aluminium chloride / benzene / 0.5 h / Heating 3: 22 percent / nitric acid, acetic acid / 4 h / 15 - 16 °C / further nitration agents 4: potassium carbonate / dimethylformamide / Ambient temperature 5: 77 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 6: 97 percent / bromine / CH2Cl2 / 0.25 h 7: 85 percent / bromine / CH2Cl2 / 19.5 h 8: 95 percent / phosphinic acid / palladized charcoal / methanol / 0.42 h / Heating 9: 1.) sodium nitrite, hydrochloric acid, 2.) phosphinic acid / 1.) dioxane, water, 0 - 5 deg C, 0.5 h, 2.) 21 h 10: 48 percent / copper bronze / 2 h / 260 °C 11: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 12: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

1: 16 percent / copper(II) nitrate trihydrate, acetic anhydride / 1.5 h / 30 °C 2: 75 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 3: 90 percent / bromine / CH2Cl2 / 0.25 h 4: 69 percent / tin(II) chloride dihydrate, hydrochloric acid / methanol / 4 h / Heating 5: 1.) isopentyl nitrite, 2.) copper(II) bromide / 1.) acetonitrile 6: 48 percent / copper bronze / 2 h / 260 °C 7: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 8: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

copper (II) chromite in quinoline T=180°C; 1.5 h;

1: 75 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 2: 90 percent / bromine / CH2Cl2 / 0.25 h 3: 69 percent / tin(II) chloride dihydrate, hydrochloric acid / methanol / 4 h / Heating 4: 1.) isopentyl nitrite, 2.) copper(II) bromide / 1.) acetonitrile 5: 48 percent / copper bronze / 2 h / 260 °C 6: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 7: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

1: potassium carbonate / dimethylformamide / Ambient temperature 2: 77 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 3: 97 percent / bromine / CH2Cl2 / 0.25 h 4: 85 percent / bromine / CH2Cl2 / 19.5 h 5: 95 percent / phosphinic acid / palladized charcoal / methanol / 0.42 h / Heating 6: 1.) sodium nitrite, hydrochloric acid, 2.) phosphinic acid / 1.) dioxane, water, 0 - 5 deg C, 0.5 h, 2.) 21 h 7: 48 percent / copper bronze / 2 h / 260 °C 8: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 9: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

1: 77 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C 2: 97 percent / bromine / CH2Cl2 / 0.25 h 3: 85 percent / bromine / CH2Cl2 / 19.5 h 4: 95 percent / phosphinic acid / palladized charcoal / methanol / 0.42 h / Heating 5: 1.) sodium nitrite, hydrochloric acid, 2.) phosphinic acid / 1.) dioxane, water, 0 - 5 deg C, 0.5 h, 2.) 21 h 6: 48 percent / copper bronze / 2 h / 260 °C 7: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 8: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

1: 58 percent / K2CO3, CuO / pyridine / 18 h / Heating 2: 1.3 g / H2, conc. HCl / Pd-C / ethyl acetate 3: 620 mg / copper(II) chromite / quinoline / 2 h / 210 °C 4: 4 percent / I2 / cyclohexane / 9 h / Irradiation View Scheme