lithium hydroxide in dichloromethane 48 h; Ambient temperature;

1: 37 percent / NBS, benzoyl peroxide / CCl4 / 0.75 h / Heating 2: 81 percent / dimethylformamide / 9 h / Heating 3: 2 percent / 5N aq. lithium hydroxide / CH2Cl2 / 48 h / Ambient temperature View Scheme

1: 81 percent / dimethylformamide / 9 h / Heating 2: 2 percent / 5N aq. lithium hydroxide / CH2Cl2 / 48 h / Ambient temperature View Scheme

1: 1.) NaNO2, 60percent HBF4 / 1.) H2O, 0 deg C, 20 min, 2.) 80 deg C, 45 min 2: 37 percent / NBS, benzoyl peroxide / CCl4 / 0.75 h / Heating 3: 81 percent / dimethylformamide / 9 h / Heating 4: 2 percent / 5N aq. lithium hydroxide / CH2Cl2 / 48 h / Ambient temperature View Scheme