sodium azide; sulfuric acid

sulfuric acid 3 h; Heating;

1: NaHCO3 / diethyl ether; H2O / 1 h / T < 5 deg C; or in benzene 2: 75 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 3: 71 percent / 70percent H2SO4 / 3 h / Heating View Scheme

1: 75 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 2: 71 percent / 70percent H2SO4 / 3 h / Heating View Scheme

1-methyl-pyrrolidin-2-one; copper(l) iodide; potassium carbonate T=100°C; Ullmann coupling;

1.1: NaH / dimethylformamide / 1 h / 0 - 4 °C 1.2: 91 percent / dimethylformamide / 20 h / 50 - 55 °C 2.1: HCl gas / ethyl acetate / 2.5 h / -5 - 0 °C 2.2: H2O / ethyl acetate / 36 h / 20 - 25 °C 3.1: 80 percent / H2SO4; EtOH; H2O / H2O / 4 h / 66 - 70 °C 4.1: 83 percent / Red-Al / toluene / 1.5 h / 60 - 62 °C 5.1: 82 percent / toluene / 80 - 90 °C 6.1: 80 percent / AlCl3 / 3 h / 170 °C 7.1: 90 percent / aq. NaOH / ethanol; H2O / Heating View Scheme

1: With tetrafluoroboric acid; sodium nitrite T=0°C; 0.5 h; 2: With copper; sodium nitrite T=20°C; 1 h; Further stages.;

acetic acid T=90°C; 1 h;

tri-tert-butyl phosphine; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) in toluene T=110°C; Buchwald-Hartwig coupling; 14 h;

sodium t-butanolate; [(t-Bu)3PH]BF4; palladium diacetate in toluene T=160°C; 3 h; microwave irradiation;