phosphorus oxytribromide in various solvent(s) T=120°C; 4 h;

1: potassium hydride (35 percent in oil), tert.-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C 2: 51 percent / tetrahydrofuran / 4 h / -78 °C View Scheme

1: 84 percent / PdCl2(Ph3P)2 / toluene / 17 h / Heating 2: 77 percent / NBS / H2O; tetrahydrofuran / 0.5 h / 20 °C 3: 64 percent / 216 h / 54 °C View Scheme

1: 84 percent / PdCl2(Ph3P)2 / toluene / 17 h / Heating 2: 77 percent / NBS / H2O; tetrahydrofuran / 0.5 h / 20 °C 3: 64 percent / 216 h / 54 °C 4: 87 percent / NaBH4 / methanol / 2 h / 20 °C View Scheme

1.1: potassium hydride / tetrahydrofuran; mineral oil / 0.67 h / 0 °C / |Inert atmosphere 1.2: 0.33 h / -78 °C / |Inert atmosphere 1.3: 0.25 h / -78 °C / |Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 60 °C / |Inert atmosphere View Scheme

1: 57 percent / 3-chloroperoxybenzoic acid / CHCl3; ethanol / 2 h / Heating 2: 60 percent / Et2N-COCl / dioxane / 16 h / 80 °C View Scheme

1: potassium hydride (35 percent in oil), tert.-BuLi / tetrahydrofuran / 1 h / -78 - 0 °C 2: 53 percent / ZnCl2, Pd(Ph3P)4 / tetrahydrofuran / 22 h / Heating View Scheme

1: With tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; ethanol T=20°C; Suzuki Coupling; 0.166667 h; Inert atmosphereSealed tube; 2: With sodium carbonate in ethylene glycol dimethyl ether; ethanol; water T=90°C; 0.25 h; Inert atmosphereSealed tubeMicrowave irradiation;

1: With tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; ethanol T=20°C; Suzuki Coupling; 0.166667 h; Inert atmosphereSealed tube; 2: With sodium carbonate in ethylene glycol dimethyl ether; ethanol; water T=90°C; 0.25 h; Inert atmosphereSealed tubeMicrowave irradiation;