carbon tetrabromide; triphenylphosphine in dichloromethane 10 h; Ambient temperature;

1: 1.) EtMgBr, 2.) CuBr / 1.)THF, reflux, 1 h, 2.) THF, reflux, 12 h 2: 87 percent / H2, ethylenediamine / P-2 nickel / ethanol / 4 h / 760 Torr 3: 97 percent / 50percent aq. TFA / CH2Cl2 / 3 h / 0 °C 4: 80 percent / PPh3 / CH2Cl2 / 1 h / 0 °C 5: 91 percent / n-BuLi / hexane; tetrahydrofuran / 1.5 h / -78 - 0 °C 6: 1.) EtMgBr, 2.) CuBr / 1.) THF, reflux, 10 min, 2.) THF, reflux, 12 h 7: 65 percent / H2 / P-2 nickel / ethanol / 5 h 8: 76 percent / CBr4, PPh3 / CH2Cl2 / 10 h / Ambient temperature View Scheme

1: 80 percent / PPh3 / CH2Cl2 / 1 h / 0 °C 2: 91 percent / n-BuLi / hexane; tetrahydrofuran / 1.5 h / -78 - 0 °C 3: 1.) EtMgBr, 2.) CuBr / 1.) THF, reflux, 10 min, 2.) THF, reflux, 12 h 4: 65 percent / H2 / P-2 nickel / ethanol / 5 h 5: 76 percent / CBr4, PPh3 / CH2Cl2 / 10 h / Ambient temperature View Scheme