1: 70 percent / fuming HNO3, fuming H2SO4 / 1,2-dichloro-ethane / 7 h / 80 - 82 °C 2: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 3: 90 percent / N2H4 / acetonitrile / 5 h / Heating 4: 94 percent / H2 / Raney Ni / ethanol / 2 h / 20 - 50 °C / 3102.9 Torr View Scheme

1: K2CO3 / 240 °C / 36775.4 Torr 2: concentrated H2SO4 View Scheme

sodium hydroxide T=290 - 310°C;

1: 87 percent / NaOH; I2; sodium acetate trihydrate / H2O / Heating 2: 96 percent / phosphoryl chloride; phosphorus pentachloride / 16 h / 100 - 110 °C View Scheme

potassium tert-butylate in tetrahydrofuran; chloroform

1: nitric acid; sulfuric acid / 96 h / 130 °C 2: thionyl chloride / N,N-dimethyl-formamide / 16 h / |Reflux View Scheme

sulfuric acid; nitric acid T=130°C; 96 h;

1.1: sodium acetate; sodium hydroxide / water / Reflux; Inert atmosphere 1.2: Inert atmosphere; Reflux 2.1: phosphorus tribromide / ethyl acetate / 4.5 h / 145 °C / Inert atmosphere 3.1: hydrogenchloride / tetrahydrofuran; diethyl ether; water / 0.08 h / 20 °C / Inert atmosphere 3.2: 24 h / Inert atmosphere; Reflux 4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 30 h / 45 °C / Inert atmosphere 5.1: copper(l) iodide; tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8.5 h / 20 °C / Inert atmosphere 6.1: hydrogen; palladium / methanol / 96 h / 20 °C 7.1: tetra-(n-butyl)ammonium iodide; caesium carbonate / N,N-dimethyl-formamide / 16 h / -20 - 20 °C / Inert atmosphere 8.1: toluene-4-sulfonic acid / methanol / 48 h / 20 °C / Inert atmosphere 8.2: 20 °C / Inert atmosphere 9.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 10.1: sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 20 °C / Inert atmosphere 11.1: nitromethane / 99.5 h / 50 - 65 °C / Inert atmosphere 12.1: palladium 10 on activated carbon; hydrogen / methanol / 24 h / 20 °C 13.1: trifluoroacetic acid / water / 2 h / 20 °C View Scheme

in chloroform Ambient temperature; Equilibrium constant;

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