1: With hydrogenchloride; sodium nitrite in 1,4-dioxane; water 2: With potassium iodide in 1,4-dioxane; water T=70 - 80°C; 0.5 h;

copper; potassium carbonate in nitrobenzene T=170°C; Ullmann reaction;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 4 h; 2: With 1-iodo-tridecafluoro-hexane in tetrahydrofuran; hexane T=-78 - 20°C;

1.1: 99 percent / AlCl3 / 22 h 2.1: 91.2 percent / SnCl2*2H2O / ethanol / 6 h / Heating 3.1: hydrochloric acid; NaNO2 / dioxane; H2O 3.2: 65.9 percent / KI / dioxane; H2O / 0.5 h / 70 - 80 °C View Scheme

1.1: KOH / 350 °C 1.2: 72 percent / 48 h / 55 °C 2.1: 99 percent / AlCl3 / 22 h 3.1: 91.2 percent / SnCl2*2H2O / ethanol / 6 h / Heating 4.1: hydrochloric acid; NaNO2 / dioxane; H2O 4.2: 65.9 percent / KI / dioxane; H2O / 0.5 h / 70 - 80 °C View Scheme

1.1: KOH / 350 °C 1.2: 72 percent / 48 h / 55 °C 2.1: 99 percent / AlCl3 / 22 h 3.1: 91.2 percent / SnCl2*2H2O / ethanol / 6 h / Heating 4.1: hydrochloric acid; NaNO2 / dioxane; H2O 4.2: 65.9 percent / KI / dioxane; H2O / 0.5 h / 70 - 80 °C View Scheme