phosphorus tribromide in dichloromethane T=0 - 20°C; 12 h;

1: 75 percent / 1.) NaH / dimethylformamide / 1.) 0 deg.C, 30 min, 2.) 30 deg.C, 3 h 2: 1.) Mg / 1.) THF, reflux, 2.5 h, 2.) THF, reflux 3 h 3: 82 percent / pyridinium chlorochromate / CH2Cl2 / 36 h / 25 °C 4: 90 percent / tetrahydrofuran / 1.) -78 deg. C, 1 h, 2.) -78 - 0 deg.C, 1 h 5: 100 percent / phosphoryl chloride / CH2Cl2 / 1 h / 25 °C 6: 91 percent / H2 / 10percent Pd/C / ethyl acetate / 48 h / 3102.9 Torr 7: 68 percent / DDQ / CH2Cl2 / 1 h View Scheme

1: With lithium aluminium tetrahydride in tetrahydrofuran 2 h; Inert atmosphereCooling with ice; 2: With Glauber's salt in tetrahydrofuran T=20°C; 2 h;

1: With borane-THF in tetrahydrofuran T=0 - 20°C; 15 h; 2: With hydrogenchloride in tetrahydrofuran; water

sodium nitrate; hydrogen bromide; copper monobromide in water; toluene

lithium aluminium tetrahydride in diethyl ether 2 h; Reflux;

1: aq. KOH 2: H2SO4 3: LiAlH4 View Scheme

sodium tetrahydroborate; aluminium trichloride; bromine 1.) CH2Cl2, 40 deg.C, 30 min, 2.) CH3OH, 0 deg.C, 2 h; Yield given. Multistep reaction;

1.1: thallium(I) trifluoroacetate; trifluoroacetic acid / 20 °C 1.2: 2 h / 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; triethylamine / ethanol / 0.33 h / 140 °C / |Microwave irradiation 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C View Scheme

Dess-Martin periodane in tetrahydrofuran T=20°C; 2 h;