PPA T=75°C; 0.666667 h;

1: 100 percent / Br2 / acetic acid / Ambient temperature 2: 86 percent / polyphosphoric acid / 0.67 h / 75 °C View Scheme

1: 90 percent / NaBH4 / methanol / 3 h / Heating 2: 78 percent / ceric ammonium nitrate / H2O; acetonitrile / 3-4 h 3: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 4: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 5: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: NaBH4 / ethanol / 12 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate / benzene / 0.5 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 - 0 °C / |Inert atmosphere 1.2: 12 h / -78 °C / |Inert atmosphere 1.3: 2 h / -78 °C / |Inert atmosphere 2.1: potassium hexacyanoferrate(III); methanesulfonamide; K2OsO4*2H2O; sodium hydrogencarbonate; potassium carbonate; (DHQD)2Pyr / water; tert-butyl alcohol / 72 h / 0 °C 3.1: sulfuric acid / 3 h / 80 °C 4.1: tetrahydrofuran / 1 h / -78 - -70 °C 5.1: hydrogenchloride / methanol / 14 h / 20 °C 6.1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane / 0.75 h / |Reflux 7.1: silver perchlorate / tetrahydrofuran / 20 °C / |Inert atmosphere 8.1: toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 0 - 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.07 h / -78 °C / |Inert atmosphere 9.2: -78 - 20 °C / |Inert atmosphere 10.1: 4-(N,N-dimethlyamino)pyridine; pyridine / 20 °C 11.1: AlCl3, aluminium chloride / nitromethane / 0.5 h / 60 °C / |Acidic conditions; |Microwave irradiation View Scheme

1: NaBH4 / ethanol / Ambient temperature 2: p-toluenesulfonic acid / benzene / 1.5 h / Heating View Scheme