1: toluene-4-sulfonic acid / chloroform / 3 h / 0 - 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 100 °C / Inert atmosphere 3: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane; water / 100 °C / Inert atmosphere 4: toluene-4-sulfonic acid / methanol / 20 °C 5: triethylamine; methanesulfonyl chloride / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 20 °C 6: trichlorophosphate / 1 h / 130 °C View Scheme

1: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 2: 63 percent / NaOEt / 7 h / Heating 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 95 percent / 170 °C 5: thionyl chloride / 0.75 h / Heating 6: 85 percent / AlCl3 / CS2 / 3 h / Heating 7: 89 percent / NaBH4 / ethanol; tetrahydrofuran 8: 96 percent / p-toluenesulfonic acid / benzene / Heating 9: 98 percent / NiCl2<dppp>2 / diethyl ether / Heating 10: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 2: 63 percent / NaOEt / 7 h / Heating 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 95 percent / 170 °C 5: thionyl chloride / 0.75 h / Heating 6: 85 percent / AlCl3 / CS2 / 3 h / Heating 7: 89 percent / NaBH4 / ethanol; tetrahydrofuran 8: 96 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 2: 63 percent / NaOEt / 7 h / Heating 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 95 percent / 170 °C 5: thionyl chloride / 0.75 h / Heating View Scheme

1: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 2: 63 percent / NaOEt / 7 h / Heating 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 95 percent / 170 °C 5: thionyl chloride / 0.75 h / Heating 6: 85 percent / AlCl3 / CS2 / 3 h / Heating 7: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

pyridinium chlorochromate

1: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 2: 63 percent / NaOEt / 7 h / Heating 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 95 percent / 170 °C 5: thionyl chloride / 0.75 h / Heating 6: 85 percent / AlCl3 / CS2 / 3 h / Heating 7: 89 percent / NaBH4 / ethanol; tetrahydrofuran 8: 96 percent / p-toluenesulfonic acid / benzene / Heating 9: 97 percent / NiCl2<dppp>2 / diethyl ether / Heating 10: 98 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

tetrakis(triphenylphosphine) palladium(0) in toluene 24 h; Heating;

1: toluene-4-sulfonic acid / chloroform / 3 h / 0 - 20 °C 2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 100 °C / Inert atmosphere 3: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane; water / 100 °C / Inert atmosphere 4: toluene-4-sulfonic acid / methanol / 20 °C 5: triethylamine; methanesulfonyl chloride / 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 20 °C View Scheme

triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine in benzene T=20°C; 12.0833 h;