N-bromosuccinmide in N,N-dimethyl-formamide T=0°C; 0.25 h;

1: 90 percent / fuming HNO3; conc. H2SO4 / 0.5 h / 0 °C 2: 80 percent / POCl3 / 24 h / Heating 3: 90 percent / SnCl2*2H2O; conc. aq. HCl / diethyl ether / 20 °C 4: 90 percent / N-bromosuccinimide / dimethylformamide / 0.25 h / 0 °C View Scheme

1: 80 percent / POCl3 / 24 h / Heating 2: 90 percent / SnCl2*2H2O; conc. aq. HCl / diethyl ether / 20 °C 3: 90 percent / N-bromosuccinimide / dimethylformamide / 0.25 h / 0 °C View Scheme

1: 90 percent / SnCl2*2H2O; conc. aq. HCl / diethyl ether / 20 °C 2: 90 percent / N-bromosuccinimide / dimethylformamide / 0.25 h / 0 °C View Scheme

1: 85 percent / K2CO3; Pd(PPh3)2Cl2 / dimethylformamide / 24 h / 100 °C 2: 90 percent / Et3N; Pd(PPh3)2Cl2; CuI / 4 h / 80 °C 3: 48 percent / CuI / dimethylformamide / 18 h / 100 °C View Scheme

bis-triphenylphosphine-palladium(II) chloride; potassium carbonate in N,N-dimethyl-formamide T=100°C; Suzuki coupling; 24 h;