1: With hydrogenchloride; sodium nitrite in ethanol; water 0.5 h; Cooling with ice; 2: With potassium iodide in water T=20°C;

1.1: 88 percent / H2 / Pd/C / aq. ethanol / 48 h / 2850.23 Torr 2.1: NaNO2 / aq. H2SO4 / 0.5 h / -5 °C 2.2: 50 percent / KI / aq. H2SO4 / 1.5 h / 0 - 20 °C View Scheme

1.1: 91 percent / trifluoroacetic anhydride / dioxane; pyridine / 0 °C 2.1: 88 percent / H2 / Pd/C / aq. ethanol / 48 h / 2850.23 Torr 3.1: NaNO2 / aq. H2SO4 / 0.5 h / -5 °C 3.2: 50 percent / KI / aq. H2SO4 / 1.5 h / 0 - 20 °C View Scheme

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine in tetrahydrofuran 20 h; Ambient temperature;

1: 1.) zinc bromide, lithium / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, 0 deg C, 2 h, ultrasonic activation; 2.) THF, room temperature, 3 h 2: sodium, ammonia / methanol; dioxane / 2 h / 80 °C / Heating View Scheme