1: aqueous NaN3 / Diazotization 2: kerosine View Scheme

1: With acetic acid; sodium nitrite in water T=0°C; 1 h; Cooling with iceInert atmosphere; 2: With sodium azide in water T=0 - 20°C; Inert atmosphere;

sulfuric acid T=-5°C;

1: sulfuric acid / -5 °C 2: concentrated H2SO4 / Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss. H3PO2 in der Waerme View Scheme

tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane in N,N-dimethyl-formamide T=20°C; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); 16 h; Inert atmosphere;

sulfuric acid; nitric acid T=0°C;

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide in tetrahydrofuran Suzuki coupling; 12 h; Reflux;

1.1: n-butyllithium / diethyl ether; pentane / 3.5 h / -40 - 0 °C / |Inert atmosphere 1.2: 6 h / -78 - 0 °C / |Inert atmosphere 2.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / |Inert atmosphere 2.2: 0.5 h / 20 °C / |Inert atmosphere 3.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere View Scheme

1.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 20 °C / |Inert atmosphere 1.2: 0.5 h / 20 °C / |Inert atmosphere 2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane / N,N-dimethyl-formamide / 16 h / 20 °C / |Inert atmosphere View Scheme

sulfuric acid T=-5°C;