hydrazine hydrate

copper(ll) bromide; isopentyl nitrite in acetonitrile T=20°C; 2 h;

sodium carbonate; tetrakis (triphenylphosphine) palladium (0) in ethanol; water; toluene

1.1: NaHCO3; AcONa / H2O 1.2: 56 percent / POCl3 / toluene / 12 h / 140 °C 2.1: 94 percent / iPentONO2; CuBr2 / acetonitrile / 2 h / 20 °C View Scheme

phosphorus pentabromide

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=85°C; Suzuki coupling; 3 h;

1: 44 percent / EtONa / ethanol 2: 89 percent / K2CO3 / aq. ethanol / 8 h / Heating 3: 85 percent / K2CO3 / dimethylformamide / Ambient temperature 4: 78 percent / NaNO2, acetic acid / ethanol / 0.5 h 5: 1.2 g / Zn, formic acid / tetrahydrofuran; H2O / 1 h / 0 - 5 °C 6: 1M KOH / methanol / Ambient temperature View Scheme

in benzene Heating;