boron tribromide in dichloromethane 12 h; Ambient temperature;

hydrogenchloride in methanol 24 h; Ambient temperature; Yield given;

1: 80 percent / lithium acetate / acetic acid / 1.5 h / Ambient temperature 2: 74 percent / N-bromosuccinimide / CCl4 / 0.5 h / Heating 3: 40 percent / sodium methoxide / tetrahydrofuran / 18 h / 0 °C 4: benzoic acid / Ambient temperature View Scheme

1: 74 percent / N-bromosuccinimide / CCl4 / 0.5 h / Heating 2: 40 percent / sodium methoxide / tetrahydrofuran / 18 h / 0 °C 3: benzoic acid / Ambient temperature View Scheme