thallous acetate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane 15 h; Heating / reflux;

hydrogenchloride in water 1 h; Heating;

1: 76 percent / I2, NaHCO3 / H2O / 3 h / 60 °C 2: 88 percent / pyridine / CHCl3 / 1.) room temp., 0.5 h, 2.) 50-60 deg C, 2 h 3: 64 percent / hexamethylphosphoric acid triamide / 3 h / 150 °C 4: 95 percent / SnCl2, HCl / diethyl ether; CH2Cl2 / 2 h 5: 1.) Mg / 1.) diethyl ether, 30 min, 2.) THF, diethyl ether, overnight, reflux 6: CrO3, conc. H2SO4 / acetone; H2O 7: 85 percent / conc. HCl / H2O / 1 h / Heating View Scheme

1: 88 percent / pyridine / CHCl3 / 1.) room temp., 0.5 h, 2.) 50-60 deg C, 2 h 2: 64 percent / hexamethylphosphoric acid triamide / 3 h / 150 °C 3: 95 percent / SnCl2, HCl / diethyl ether; CH2Cl2 / 2 h 4: 1.) Mg / 1.) diethyl ether, 30 min, 2.) THF, diethyl ether, overnight, reflux 5: CrO3, conc. H2SO4 / acetone; H2O 6: 85 percent / conc. HCl / H2O / 1 h / Heating View Scheme

1: 64 percent / hexamethylphosphoric acid triamide / 3 h / 150 °C 2: 95 percent / SnCl2, HCl / diethyl ether; CH2Cl2 / 2 h 3: 1.) Mg / 1.) diethyl ether, 30 min, 2.) THF, diethyl ether, overnight, reflux 4: CrO3, conc. H2SO4 / acetone; H2O 5: 85 percent / conc. HCl / H2O / 1 h / Heating View Scheme

1: 95 percent / SnCl2, HCl / diethyl ether; CH2Cl2 / 2 h 2: 1.) Mg / 1.) diethyl ether, 30 min, 2.) THF, diethyl ether, overnight, reflux 3: CrO3, conc. H2SO4 / acetone; H2O 4: 85 percent / conc. HCl / H2O / 1 h / Heating View Scheme

1: 1.) Mg / 1.) diethyl ether, 30 min, 2.) THF, diethyl ether, overnight, reflux 2: CrO3, conc. H2SO4 / acetone; H2O 3: 85 percent / conc. HCl / H2O / 1 h / Heating View Scheme

iodine; mercury(II) oxide in acetic acid 1 h; Ambient temperature;

bromine in acetic acid Yield given;