N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 9 h; Heating;

1.1: 95 percent / Zn / methanol / 4 h / 23 °C 2.1: 48 percent HBr / H2O / 2 h 2.2: NaNO2 / H2O 2.3: 72 percent / CuBr; 48 percent HBr / H2O / 2 h / Heating 3.1: 92 percent / NBS; BPO / CCl4 / 9 h / Heating View Scheme

1.1: 48 percent HBr / H2O / 2 h 1.2: NaNO2 / H2O 1.3: 72 percent / CuBr; 48 percent HBr / H2O / 2 h / Heating 2.1: 92 percent / NBS; BPO / CCl4 / 9 h / Heating View Scheme

1: sulfuric acid; nitric acid / 1 h / 20 °C / Inert atmosphere; Cooling with ice 2: zinc / methanol / 4 h / 20 °C / Inert atmosphere 3: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 5 h / 70 °C / Reflux; Inert atmosphere 4: N-bromosuccinmide; dibenzoyl peroxide / tetrachloromethane / 9 h / 90 °C / Inert atmosphere View Scheme

trimethylamine-N-oxide in dichloromethane; dimethyl sulfoxide T=28°C; 8 h;