1: 1.) sec-BuLi, TMEDA, 2.) I2 / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, -20 deg C, 10 min 2: 81 percent / K2CO3, CuCl / propan-2-ol / 1.5 h / Heating 3: 69 percent / K2CO3 / dimethylformamide / 3 h / 20 - 45 °C 4: 1.) POCl3, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h 5: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature 6: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating View Scheme