bromine; iodine 24 h; Ambient temperature;

1: 1.) Mg, I2, 2.) Ni(Ph2PCH2CH2CH2PPh2)Cl2 / 1.) Et2O, reflux, 30 min, 2.) Et2O, THF, reflux, 24 h 2: 84 percent / Br2, I2 / 24 h / 0 °C View Scheme

1: 93 percent / <1,3-bis(diphenylphosphino)propane>Cl2Ni / diethyl ether / 24 h / Heating 2: 93 percent / Br2, I2 / 24 h / Ambient temperature View Scheme

1: 1.) Mg, I2, 2.) Ni(Ph2PCH2CH2CH2PPh2)Cl2 / 1.) Et2O, reflux, 30 min, 2.) Et2O, THF, reflux, 24 h 2: 84 percent / Br2, I2 / 24 h / 0 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -60 °C 1.2: tetrahydrofuran; hexane / 1 h / -60 - 20 °C 2.1: p-toluenesulfonic acid / benzene / 5 h / Heating 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -70 °C 3.2: tetrahydrofuran; hexane / -70 - 20 °C 4.1: p-toluenesulfonic acid / benzene / 2 h / Heating 5.1: 91 percent / trifluoroacetic acid / H2O / Heating View Scheme

1: 1,4-dibromo-2,5-di-n-octylbenzene With n-butyllithium in tetrahydrofuran; hexane T=-60°C; 0.25 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-60 - 20°C; 1 h;

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-butyllithium / tetrahydrofuran; hexane / 0.25 h / -60 °C 1.2: tetrahydrofuran; hexane / 1 h / -60 - 20 °C 2.1: p-toluenesulfonic acid / benzene / 5 h / Heating 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -70 °C 3.2: tetrahydrofuran; hexane / -70 - 20 °C 4.1: p-toluenesulfonic acid / benzene / 2 h / Heating View Scheme