1: diethyl malonate With sodium hydride T=0 - 20°C; 2: 1-iodo-2-(2-iodoethyl)-benzene in tetrahydrofuran T=20°C; 3: With sodium chloride in water; dimethyl sulfoxide T=150°C;

1: diethyl malonate With sodium hydride in tetrahydrofuran T=0°C; 1 h; 2: 2-(2'-bromoethyl)-1-iodobenzene in tetrahydrofuran T=20°C; 3 h;

1.1: BH3*S(CH3)2 / tetrahydrofuran / 0 - 20 °C 2.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 20 °C 3.1: sodium hydride / 0 - 20 °C 3.2: 20 °C 3.3: 150 °C View Scheme

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 0 - 20 °C 2.1: sodium hydride / 0 - 20 °C 2.2: 20 °C 2.3: 150 °C View Scheme

1.1: water; sodium chloride / dimethyl sulfoxide / 150 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -50 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 3.2: -78 - 20 °C View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium hydride 1.) DMF, 0 deg C, 2.) from 130 to 135 deg C; Yield given. Multistep reaction;