potassium carbonate in methanol; dichloromethane T=20°C;

1.1: CuI; triethylamine / Pd(PPh3)2Cl2 / cooling 1.2: potassium carbonate / methanol; CH2Cl2 / 20 °C 1.3: triethylamine; CuI / Pd(PPh3)2Cl2 2.1: n-BuLi / tetrahydrofuran; hexane / -78.15 - -40.15 °C 2.2: 91 percent / I2 / tetrahydrofuran; hexane / -78.15 - 19.85 °C 3.1: 81 percent / potassium carbonate / methanol; CH2Cl2 / 20 °C View Scheme

1.1: 62 percent / bromine; iodine 2.1: n-BuLi / tetrahydrofuran; hexane / -78.15 - -40.15 °C 2.2: 78 percent / I2 / tetrahydrofuran; hexane / -78.15 - 19.85 °C 3.1: CuI; triethylamine / Pd(PPh3)2Cl2 / cooling 3.2: potassium carbonate / methanol; CH2Cl2 / 20 °C 3.3: triethylamine; CuI / Pd(PPh3)2Cl2 4.1: n-BuLi / tetrahydrofuran; hexane / -78.15 - -40.15 °C 4.2: 91 percent / I2 / tetrahydrofuran; hexane / -78.15 - 19.85 °C 5.1: 81 percent / potassium carbonate / methanol; CH2Cl2 / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78.15 - -40.15 °C 1.2: 78 percent / I2 / tetrahydrofuran; hexane / -78.15 - 19.85 °C 2.1: CuI; triethylamine / Pd(PPh3)2Cl2 / cooling 2.2: potassium carbonate / methanol; CH2Cl2 / 20 °C 2.3: triethylamine; CuI / Pd(PPh3)2Cl2 3.1: n-BuLi / tetrahydrofuran; hexane / -78.15 - -40.15 °C 3.2: 91 percent / I2 / tetrahydrofuran; hexane / -78.15 - 19.85 °C 4.1: 81 percent / potassium carbonate / methanol; CH2Cl2 / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78.15 - -40.15 °C 1.2: 91 percent / I2 / tetrahydrofuran; hexane / -78.15 - 19.85 °C 2.1: 81 percent / potassium carbonate / methanol; CH2Cl2 / 20 °C View Scheme