1: 75 percent / Na2CO3 / Pd(PPh3)4 / toluene; ethanol / 12 h / Heating 2: 1.) n-butyllithium, 2,2,6,6-tetramethylpiperidine / 1.) hexane, 0 degC, 30 min, THF, -70 degC, 1.5 h; 2.) -70 degC, 2 h 3: 96 percent / 57percent hydroiodic acid / 5 h / 80 °C 4: 94 percent / phopsphorus oxychloride / 6 h / 90 °C 5: 69 percent / 2 h / 170 °C View Scheme

T=170°C; 2 h;

1: 1.) n-butyllithium, 2,2,6,6-tetramethylpiperidine / 1.) hexane, 0 degC, 30 min, THF, -70 degC, 1.5 h; 2.) -70 degC, 2 h 2: 96 percent / 57percent hydroiodic acid / 5 h / 80 °C 3: 94 percent / phopsphorus oxychloride / 6 h / 90 °C 4: 69 percent / 2 h / 170 °C View Scheme

1: 94 percent / phopsphorus oxychloride / 6 h / 90 °C 2: 69 percent / 2 h / 170 °C View Scheme

1: 96 percent / 57percent hydroiodic acid / 5 h / 80 °C 2: 94 percent / phopsphorus oxychloride / 6 h / 90 °C 3: 69 percent / 2 h / 170 °C View Scheme