potassium fluoride; N-hexadecyl-N,N,N-trimethylammonium bromide in N,N-dimethyl-formamide T=125°C;

sulfuric acid; nitric acid T=50°C;

potassium fluoride in anhydrous xylene

1: water; copper (I)-chloride; concentrated aqueous hydrochloric acid / 0 °C 2: sulfuric acid; nitric acid / 50 °C View Scheme

1: 80 percent / H2 / Pd/C / ethanol / 6 h / 80 °C / 5250.4 Torr 2: NaNO2 View Scheme

hydrogen; palladium on activated charcoal in ethanol T=80°C; P=5250.4 Torr; 6 h;

iron

1: N,N-dimethyl-formamide / 12 h / 100 °C 2: hydrogenchloride; acetic acid / water / 18 h / |Reflux 3: thionyl chloride / 4 h / 20 °C 4: acetic acid; hydrogen / 3 h / 20 °C / 2327.23 Torr 5: sodium tetrahydroborate; lithium bromide; boric acid trimethyl ester / tetrahydrofuran / 18 h / |Reflux 6: triphenylphosphine / tetrahydrofuran; tetrachloromethane / 3 h / |Reflux View Scheme

1: dimethylformamide / 20 °C 2: 60 percent / MgCl2*6H2O / N,N-dimethyl-acetamide / 7 h / 140 - 150 °C View Scheme

1: N,N-dimethyl-formamide / 12 h / 100 °C 2: sodium chloride / water; dimethyl sulfoxide / 12 h / 160 °C View Scheme