bromine T=185 - 190°C;

phosphorus tribromide 3 h; Heating;

T=185 - 190°C;

1: 1.9 g / toluene / 0.67 h / 0 °C 2: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature 3: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 4: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr View Scheme

1: 1.9 g / toluene / 0.67 h / 0 °C 2: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature 3: 78 percent / hexamethylphosphoramide, LiN(TMS)2 / tetrahydrofuran / 0.75 h / -78 °C 4: 100 percent / H2 / PdCl2 / ethanol; tetrahydrofuran; methanol / 20 h / 2585.7 Torr 5: 1.29 g / NaHCO3 / H2O; dioxane / 3 h / Ambient temperature 6: 1.19 g / bis(trimethylsilyl)trifluoroacetamide, iodotrimethylsilane / CH2Cl2 / -20 - 20 °C View Scheme

in diethyl ether T=20°C; 3.5 h; Inert atmosphere;

Na2O2 in diethyl ether; water T=0 - 20°C; 2 h;

formic acid T=30 - 35°C;

1: 1.9 g / toluene / 0.67 h / 0 °C 2: 52 percent / (diethylamido)sulfur trifluoride / Ambient temperature View Scheme

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