tetra-(n-butyl)ammonium iodide in dichloromethane; water 8 h;

pyridine; thionyl bromide in dichloromethane 3 h; Heating;

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane Irradiation;

1: 95 percent / imidazole / dimethylformamide / Ambient temperature 2: 1.) 1.4M sec-butyllithium / 1.) THF, cyclohexane, 30 min at -78 deg C; 2.) THF, cyclohexane, 30 min at room temp. 3: 85 percent / KF / dimethylformamide / 18 h / Ambient temperature 4: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 5: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating View Scheme

1: 85 percent / KF / dimethylformamide / 18 h / Ambient temperature 2: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 3: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating View Scheme

1: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 2: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating View Scheme

1: 1.) 1.4M sec-butyllithium / 1.) THF, cyclohexane, 30 min at -78 deg C; 2.) THF, cyclohexane, 30 min at room temp. 2: 85 percent / KF / dimethylformamide / 18 h / Ambient temperature 3: 83 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 4: 95 percent / pyridine, SOBr2 / CH2Cl2 / 3 h / Heating View Scheme

1: 1.) lithium diisopropylamide / 1.) THF, hexane, 40 min, -78 deg C; 2.) THF, hexane, 18 h at room temp. 2: 55percent HI / 1.5 h / Heating View Scheme