n-butyllithium; iodine; diisopropylamine in tetrahydrofuran; hexane T=-75°C; 2 h;

n-butyllithium; nitrobenzene; copper(ll) bromide in diethyl ether; hexane T=-75 - 25°C;

1: 79 percent / BuLi; CuBr2; PhNO2 / diethyl ether; hexane / -75 - 25 °C 2: 86 percent / BuLi / hexane; diethyl ether / -100 - 25 °C 3: 89 percent / NaBH4 / methanol; tetrahydrofuran / 12 h / 25 °C 4: 81 percent / Ph3P; Br2 / acetonitrile / 6 h / 50 °C View Scheme

1: 79 percent / BuLi; CuBr2; PhNO2 / diethyl ether; hexane / -75 - 25 °C 2: 86 percent / BuLi / hexane; diethyl ether / -100 - 25 °C 3: 89 percent / NaBH4 / methanol; tetrahydrofuran / 12 h / 25 °C 4: 92 percent / 1H-imidazole / dimethylformamide / 20 h / 25 °C 5: 74 percent / BuLi / hexane; tetrahydrofuran / -75 °C 6: 85 percent / Bu4NF / tetrahydrofuran / 0.25 h / 25 °C 7: 78 percent / Ph3P; Br2 / acetonitrile / 6 h / 50 °C View Scheme

1: 79 percent / BuLi; CuBr2; PhNO2 / diethyl ether; hexane / -75 - 25 °C 2: 86 percent / BuLi / hexane; diethyl ether / -100 - 25 °C 3: 89 percent / NaBH4 / methanol; tetrahydrofuran / 12 h / 25 °C 4: 92 percent / 1H-imidazole / dimethylformamide / 20 h / 25 °C 5: 83 percent / Bu4NF / tetrahydrofuran / 0.25 h / 25 °C 6: 77 percent / Ph3P; Br2 / acetonitrile / 6 h / 50 °C View Scheme