1.1: 65 percent / Cu; Pd(PPh3)4 / dimethylsulfoxide / 4 h / 110 °C 2.1: Zn; TiCl4 / tetrahydrofuran / 0 - 20 °C 2.2: 56 percent / tetrahydrofuran / 2 h / 80 °C View Scheme

1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 4 h / 80 °C / |Inert atmosphere 2: titanium tetrachloride; zinc; pyridine; tetrahydrofuran / 4 h / |Reflux View Scheme

phosphorus tribromide