in N,N-dimethyl-formamide T=100°C; 8 h; Sealed tubeInert atmosphere;

phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide 1.5 h; Ambient temperature;

1: 82 percent / NaNO2, Br2, 48percent HBr / 5 °C 2: 43 percent / Cu, HMPA / 112 - 130 °C / autoclave 3: 21 percent / KMnO4 / H2O / Heating 4: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 5: 36 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 43 percent / Cu, HMPA / 112 - 130 °C / autoclave 2: 21 percent / KMnO4 / H2O / Heating 3: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 4: 36 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 21 percent / KMnO4 / H2O / Heating 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 36 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme

1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 36 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme