1: 98 percent / Pd(PPh3)4, aq. Na2CO3 / toluene; ethanol / 4 h / 110 °C 2: 98 percent / NBS / CCl4 / 1 h 3: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 1 h, 2.) Et2O, hexane, RT, 12 h 4: 46 percent / Et3N, PPh3, CCl4 / acetonitrile / 1.) RT, 1 h, 2.) reflux, 3 h 5: 62 percent / 1,2-dichloro-benzene / 8 h / Heating 6: 41 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 4 h / Heating 7: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C 8: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating View Scheme