copper(l) iodide; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride 8 h; Heating;

1: Br2; AcOH 2: 87 percent / KOH / dimethylsulfoxide / 22 h / 20 °C 3: 93 percent / NaBr; AcOH; H2SO4 / 8 h / 76 °C 4: 96 percent / AcOH / 6 h / Heating 5: 86 percent / aq. KOH / methanol; tetrahydrofuran / 5.5 h / Heating 6: 76.5 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Heating 7: CuI; iPr2NH / Pd(PPh3)4 / toluene View Scheme

1: 87 percent / KOH / dimethylsulfoxide / 22 h / 20 °C 2: 93 percent / NaBr; AcOH; H2SO4 / 8 h / 76 °C 3: 96 percent / AcOH / 6 h / Heating 4: 86 percent / aq. KOH / methanol; tetrahydrofuran / 5.5 h / Heating 5: 76.5 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Heating 6: CuI; iPr2NH / Pd(PPh3)4 / toluene View Scheme

1: KOH / dimethylsulfoxide 2: BuLi / diethyl ether 3: CuI; iPr2NH / Pd(PPh3)4 / toluene View Scheme

1: 93 percent / NaBr; AcOH; H2SO4 / 8 h / 76 °C 2: 96 percent / AcOH / 6 h / Heating 3: 86 percent / aq. KOH / methanol; tetrahydrofuran / 5.5 h / Heating 4: 76.5 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Heating 5: CuI; iPr2NH / Pd(PPh3)4 / toluene View Scheme

potassium fluoride in tetrahydrofuran; methanol T=20°C; 6 h;