1: 1.) Mg, 1,2-dibromotetrafluoroethane / 1) THF, 1 h; 2) THF, 50-60 deg C, 4-6 h 2: 1.) H2SO4, 2.) H2 / 2.) Pd/C / 1) EtOH, reflux, overnight; 2) EtOH, rt, 4 h View Scheme

n-butyllithium in tetrahydrofuran T=-78 - 0°C;

1: sec-BuLi / tetrahydrofuran / -78 °C 2: BrF2CCF2Br, TMEDA / tetrahydrofuran / -78 - 0 °C 3: 95 percent / TFA / CH2Cl2 4: 99 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C View Scheme

1: 95 percent / TFA / CH2Cl2 2: 99 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C View Scheme