boron tribromide in dichloromethane 4 h; Ambient temperature;

1: 1.) n-BuLi / 1.) THF, 0 deg C, 3 h, 2.) 0 deg C to RT, 12 h 2: 2,2'-azobis(2-methylpropionitrile) (AIBN) / 3 h / Heating 3: 2,2'-azobis(2-methylpropionitrile) (AIBN), Bu3SnH / toluene / 3 h / Heating 4: 0.848 g / BBr3 / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 89 percent / CBr4, Ph3P / acetonitrile / 24 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, 0 deg C, 3 h, 2.) 0 deg C to RT, 12 h 3: 2,2'-azobis(2-methylpropionitrile) (AIBN) / 3 h / Heating 4: 2,2'-azobis(2-methylpropionitrile) (AIBN), Bu3SnH / toluene / 3 h / Heating 5: 0.848 g / BBr3 / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, 0 deg C, 3 h, 2.) 0 deg C to RT, 12 h 2: 2,2'-azobis(2-methylpropionitrile) (AIBN) / 3 h / Heating 3: 2,2'-azobis(2-methylpropionitrile) (AIBN), Bu3SnH / toluene / 3 h / Heating 4: 0.848 g / BBr3 / CH2Cl2 / 4 h / Ambient temperature View Scheme

1: 2,2'-azobis(2-methylpropionitrile) (AIBN) / 3 h / Heating 2: 2,2'-azobis(2-methylpropionitrile) (AIBN), Bu3SnH / toluene / 3 h / Heating 3: 0.848 g / BBr3 / CH2Cl2 / 4 h / Ambient temperature View Scheme