sulfuric acid; sodium nitrite; Sandmayer catalyst in acetic acid T=60°C; Sandmayer reaction; 0.5 h;

1: 41 percent / tBuLi / tetrahydrofuran; pentane / 2.5 h / -20 °C 2: 66 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 3: 94 percent / HCl / dioxane / 2.5 h / 20 °C 4: 62 percent / NaNO2; H2SO4 / Sandmayer catalyst / acetic acid / 0.5 h / 60 °C View Scheme

1: 66 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 2: 94 percent / HCl / dioxane / 2.5 h / 20 °C 3: 62 percent / NaNO2; H2SO4 / Sandmayer catalyst / acetic acid / 0.5 h / 60 °C View Scheme

1: 94 percent / HCl / dioxane / 2.5 h / 20 °C 2: 62 percent / NaNO2; H2SO4 / Sandmayer catalyst / acetic acid / 0.5 h / 60 °C View Scheme