1.1: 92 percent / NaI / acetone / 20 °C 2.1: Zn; 1,2-dibromoethane; Me3SiCl / dimethylformamide / 2 h / 35 °C 2.2: 60 percent / Pd(PPh3)2Cl2 / dimethylformamide 3.1: 85 percent / aq. LiOH / tetrahydrofuran / 20 °C View Scheme

sodium iodide in acetone T=20°C;

1.1: 92 percent / NaI / acetone / 20 °C 2.1: Zn; 1,2-dibromoethane; Me3SiCl / dimethylformamide / 2 h / 35 °C 2.2: 57 percent / Pd(PPh3)2Cl2 / dimethylformamide 3.1: 60 percent / aq. LiOH / tetrahydrofuran / 20 °C View Scheme

1.1: lithium triethylborohydride / tetrahydrofuran / 0 °C / Inert atmosphere 1.2: 0 °C 2.1: trimethyl tin hydroxide / 1,2-dichloro-ethane / 1 h / Inert atmosphere; Reflux View Scheme