potassium fluoride; copper(l) iodide in 1-methyl-pyrrolidin-2-one T=50°C; 20 h;

1: 56 percent / aluminium chloride / chlorobenzene / 2 h / 125 °C 2: 83 percent / phosphorus oxychloride / 2 h / 125 °C 3: 79 percent / diisopropylamine; butyllithium; iodine / tetrahydrofuran; hexane / 2 h / -75 °C 4: 64 percent / copper iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 20 h / 50 °C View Scheme

1: 92 percent / potassium carbonate / acetone; H2O / 2 h / 0 °C 2: 56 percent / aluminium chloride / chlorobenzene / 2 h / 125 °C 3: 83 percent / phosphorus oxychloride / 2 h / 125 °C 4: 79 percent / diisopropylamine; butyllithium; iodine / tetrahydrofuran; hexane / 2 h / -75 °C 5: 64 percent / copper iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 20 h / 50 °C View Scheme

1: 79 percent / diisopropylamine; butyllithium; iodine / tetrahydrofuran; hexane / 2 h / -75 °C 2: 64 percent / copper iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 20 h / 50 °C View Scheme

1: 83 percent / phosphorus oxychloride / 2 h / 125 °C 2: 79 percent / diisopropylamine; butyllithium; iodine / tetrahydrofuran; hexane / 2 h / -75 °C 3: 64 percent / copper iodide; potassium fluoride / 1-methyl-pyrrolidin-2-one / 20 h / 50 °C View Scheme