1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT, 12 h 2: 83 percent / NBS / CCl4 / 1 h / Ambient temperature 3: 98 percent / Pd(PPh3)4, aq. Na2CO3 / toluene; ethanol / 4 h / 110 °C 4: 98 percent / NBS / CCl4 / 1 h 5: 1.) n-BuLi / 1.) Et2O, hexane, -78 deg C, 1 h, 2.) Et2O, hexane, RT, 12 h 6: 46 percent / Et3N, PPh3, CCl4 / acetonitrile / 1.) RT, 1 h, 2.) reflux, 3 h 7: 62 percent / 1,2-dichloro-benzene / 8 h / Heating 8: 41 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 4 h / Heating 9: 93 percent / 28percent NH4OH / methanol / 48 h / 150 °C 10: 80 percent / sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 0.5 h / Heating View Scheme

potassium hydroxide in dimethyl sulfoxide T=18 - 20°C; 2 h;