hydrogenchloride; sodium azide; sodium acetate; sodium nitrite 1.) 3-5 deg C, 2.) water, 30 min; Yield given. Multistep reaction;

hydrogenchloride; sodium azide; sodium acetate; sodium nitrite 1.) -5 deg C, 3 min, 2.) water, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

1.1: potassium acetate; acetic acid / 1 h / 20 °C 1.2: 20 °C 2.1: tin(ll) chloride / ethanol; water / 2 h / Reflux View Scheme

1: tetrafluoroboric acid / toluene / 120 °C / |Inert atmosphere 2: tetrahydrofuran / 20 °C / |Inert atmosphere 3: acetic acid; iron / 3 h / 90 °C / |Inert atmosphere 4: 24 h / 120 °C / |Inert atmosphere 5: tert.-butyl lithium; carbon tetrabromide / -78 °C 6: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine; potassium phosphate / 1,4-dioxane / 1 h / 120 °C / |Inert atmosphere; |Microwave irradiation 7: hydrogenchloride / tetrahydrofuran / 20 °C / |Inert atmosphere View Scheme

1: 87 percent / NaNO2, HBF4 (34percent) / H2O / 0.5 h / -8 - -2 °C 2: 115 - 120 °C 3: 77 percent / ethanol / 16 h / Heating 4: H2 / Pd-C, 10percent / ethanol / 1 h 5: 50 percent / PPA / 120 °C View Scheme

1: With bromine; sodium acetate in acetic acid 2: With sodium hydrogencarbonate T=0°C; pH=~ 7;

1: 87 percent / NaNO2, HBF4 (34percent) / H2O / 0.5 h / -8 - -2 °C 2: 115 - 120 °C 3: 80 percent / hydrazine hydrate / ethanol / 1 h / 0 °C View Scheme

1: tetrafluoroboric acid / toluene / 120 °C / |Inert atmosphere 2: tetrahydrofuran / 20 °C / |Inert atmosphere 3: acetic acid; iron / 3 h / 90 °C / |Inert atmosphere 4: 24 h / 120 °C / |Inert atmosphere View Scheme

1: tetrafluoroboric acid / toluene / 120 °C / |Inert atmosphere 2: tetrahydrofuran / 20 °C / |Inert atmosphere 3: acetic acid; iron / 3 h / 90 °C / |Inert atmosphere View Scheme