1.1: 94 percent / KOH / ethanol; H2O / 3 h / 100 - 110 °C 2.1: 96 percent / copper powder / quinoline / 3 h / Heating 3.1: 96 percent / DMAP / acetonitrile / 0 - 20 °C 4.1: NBS; AIBN / CCl4 / 2.5 h / Heating 5.1: 5.37 g / nBuLi / tetrahydrofuran; hexane / 5 h / -78 °C 6.1: HCl / tetrahydrofuran; H2O / 2 h / 20 °C 6.2: 71 percent / HCl / ethyl acetate / 3 h / 0 °C 7.1: 96 percent / NaOH / ethanol; H2O / 1 h / 40 °C View Scheme

1: 94 percent / KOH / ethanol; H2O / 3 h / 100 - 110 °C 2: 96 percent / copper powder / quinoline / 3 h / Heating View Scheme