1: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl2(PPh3)2 / 18 h / 110 °C / 7600 Torr 2: 95 percent / 10percent NaOH / 1 h / Heating 3: 80 percent / HCl / 4 h 4: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 5: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 6: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl2(PPh3)2 / 18 h / 110 °C / 7600 Torr 2: 95 percent / 10percent NaOH / 1 h / Heating View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: 80 percent / bromine-dioxane complex / dioxane<br />2: 80 percent / cuprous iodide / dimethylformamide / 1 h / 100 &deg;C<br />3: 95 percent / sulfuric acid / 0.08 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 80 percent / Br₂*dioxane / dioxane / 1 h / 5 - 10 &deg;C<br />2: 80 percent / Na, CuI / dimethylformamide / 1 h / 100 &deg;C<br />3: 95 percent / sulfuric acid / 0.08 h<br /> <br /> &nbsp;