water; hydrogen bromide 4 h; Heating;

1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 2 h; 2.) THF, hexane, -70 deg C, 1 h, 0 deg C, 2 h 2: 98.2 percent / activated MnO2 / acetone / 0.5 h / Heating 3: 69.7 percent / HBr/AcOH / CH2Cl2 / 6 h / Ambient temperature 4: 94.6 percent / 65percent HNO3 / acetic acid / 1.5 h / Ambient temperature 5: 84.8 percent / 48percent HBr/H2O / 4 h / Heating View Scheme

1: 1.) BuLi / 1.) THF, hexane, -70 deg C, 2 h; 2.) THF, hexane, -70 deg C, 1 h, 0 deg C, 2 h 2: 98.2 percent / activated MnO2 / acetone / 0.5 h / Heating 3: 69.7 percent / HBr/AcOH / CH2Cl2 / 6 h / Ambient temperature 4: 94.6 percent / 65percent HNO3 / acetic acid / 1.5 h / Ambient temperature 5: 84.8 percent / 48percent HBr/H2O / 4 h / Heating View Scheme

1: 94.6 percent / 65percent HNO3 / acetic acid / 1.5 h / Ambient temperature 2: 84.8 percent / 48percent HBr/H2O / 4 h / Heating View Scheme

1: 69.7 percent / HBr/AcOH / CH2Cl2 / 6 h / Ambient temperature 2: 94.6 percent / 65percent HNO3 / acetic acid / 1.5 h / Ambient temperature 3: 84.8 percent / 48percent HBr/H2O / 4 h / Heating View Scheme