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

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

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

1: 95 percent / phosphinic acid / palladized charcoal / methanol / 0.42 h / Heating 2: 1.) sodium nitrite, hydrochloric acid, 2.) phosphinic acid / 1.) dioxane, water, 0 - 5 deg C, 0.5 h, 2.) 21 h 3: 48 percent / copper bronze / 2 h / 260 °C 4: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating 5: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C View Scheme

hydrogen bromide; acetic acid 36 h; Heating;

1: 85 percent / I2, silver trifluoroacetate / CHCl3 2: 81 percent / copper bronze / 4.5 h / 200 °C 3: 73 percent / 48percent HBr, glacial acetic acid / 36 h / Heating View Scheme

1: 97 percent / potassium carbonate / dimethylformamide / 14 h / Ambient temperature 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

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: 620 mg / copper(II) chromite / quinoline / 2 h / 210 °C 2: 4 percent / I2 / cyclohexane / 9 h / Irradiation View Scheme