1: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 2: 99 percent / AgNO3 / acetone; H2O / 2 h / Ambient temperature View Scheme

1: 69 percent / BH3 / tetrahydrofuran / 6 h / 0 °C 2: 64 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 3: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 4: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 5: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 6: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 7: 99 percent / AgNO3 / acetone; H2O / 2 h / Ambient temperature View Scheme

1: 100 percent / CF3COOH / CH2Cl2 / 12 h / 0 °C 2: 69 percent / BH3 / tetrahydrofuran / 6 h / 0 °C 3: 64 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 4: 46 percent / diethyl ether; tetrahydrofuran / 2 h / -78 °C 5: 85 percent / pyridinium chlorochromate, Celite / CH2Cl2 / 3 h / Ambient temperature 6: 34 percent / ethanol; tetrahydrofuran / 2 h / -78 °C 7: 78 percent / Br2, azobisisobutylonitrile / CCl4 / 2 h / 70 °C 8: 99 percent / AgNO3 / acetone; H2O / 2 h / Ambient temperature View Scheme

pyridine; zinc 1 h; Ambient temperature;

potassium hydroxide T=0°C;