1: 98 percent / AgNO3 / acetonitrile / 12 h 2: 88 percent / NaOAc*3H2O, DMSO / 0.42 h / Ambient temperature 3: 62 percent / conc. aq. HCl / ethanol / 4.5 h / 80 °C View Scheme

1: ethylene dibromide; zinc With lithium chloride in tetrahydrofuran Heating; 2: acetic acid 4-chloromethyl-phenyl ester in tetrahydrofuran Heating; 3: monobromoacetic acid chloride; C8H7ClO2Zn With Li2Cu(CN)Cl2 in tetrahydrofuran T=-80 - 25°C; Negishi coupling reaction; Inert atmosphere;

hydrogen bromide T=0°C; 0.5 h; Yield given;

1: 84 percent / NaOAc / 2 h / Heating 2: SOCl2 / 12 h / Ambient temperature 3: diethyl ether / 1.5 h / 0 °C 4: HBr / 0.5 h / 0 °C View Scheme

1: diethyl ether / 1.5 h / 0 °C 2: HBr / 0.5 h / 0 °C View Scheme

1: SOCl2 / 12 h / Ambient temperature 2: diethyl ether / 1.5 h / 0 °C 3: HBr / 0.5 h / 0 °C View Scheme

1: 98 percent / AgNO3 / acetonitrile / 12 h 2: 88 percent / NaOAc*3H2O, DMSO / 0.42 h / Ambient temperature View Scheme