hydrogen; palladium on activated charcoal in methanol; ethyl acetate T=22°C; 12 h;

1: 82 percent / NaH / tetrahydrofuran / 1.5 h / 0 - 22 °C 2: 99 percent / H2 / Pd/C / methanol; ethyl acetate / 12 h / 22 °C View Scheme

1.1: 99 percent / 4 h / 40 °C 2.1: n-BuLi; TMSCl / pentane / 0.25 h / -78 °C 2.2: n-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C 2.3: 54 percent / aq. HCl / 0.5 h / 22 °C 3.1: 83 percent / 1,2-dichloro-benzene / 0.08 h / 205 °C / microwave irradiation View Scheme