palladium diacetate; cesium fluoride in ethylene glycol dimethyl ether; water Suzuki coupling; 3 h; Reflux;

1: 83 percent / hydroxylamine hydrochloride; sodium sulfate; aq. HCl / 55 °C 2: 80 percent / conc. sulfuric acid / 55 - 80 °C 3: 74 percent / aq. sodium bicarbonate / tetrakis[triphenylphosphine]palladium / 1,2-dimethoxy-ethane / Heating View Scheme

sulfuric acid 4 h; Ambient temperature;

1: 50 percent / aq. H2SO4 / 0.25 h / 80 °C 2: 55 percent / Pd(PPh3)4; NaHCO3 / 1,2-dimethoxy-ethane; H2O / 5 h / Heating View Scheme

1: 49 percent 2: 29 percent / isoamyl nitrite / CH2Cl2; tetrahydrofuran / 1.5 h / Heating 3: 30 percent / conc. HCl / methanol / 16 h / Heating View Scheme

1: With dihydrogen peroxide; sodium hydroxide in water T=20 - 50°C; 1 h; 2: With hydrogenchloride in water pH=3 - 4;

1: 49 percent 2: 29 percent / isoamyl nitrite / CH2Cl2; tetrahydrofuran / 1.5 h / Heating 3: 20 percent / conc. HCl / methanol / 16 h / Heating View Scheme