1: With hydrogenchloride; hydrogen; palladium hydroxide - carbon; water in methanol T=50°C; P=2585.74 Torr; 20 h; 2: With sodium t-butanolate in methanol T=20°C; 20 h;

1.1: 83 percent / I2 / ZnI2 / CH2Cl2 / 20 h / Heating 2.1: hydrogen; aq. HCl / Pearlman's catalyst Pd(OH)2/C/H2O / methanol / 20 h / 50 °C / 2585.74 Torr 2.2: 11.2 g / NaOtBu / methanol / 20 h / 20 °C View Scheme

1.1: H2SO4 / 1.5 h / 70 °C 1.2: 80 percent / 20 h / 0 - 20 °C 2.1: 83 percent / I2 / ZnI2 / CH2Cl2 / 20 h / Heating 3.1: hydrogen; aq. HCl / Pearlman's catalyst Pd(OH)2/C/H2O / methanol / 20 h / 50 °C / 2585.74 Torr 3.2: 11.2 g / NaOtBu / methanol / 20 h / 20 °C View Scheme