palladium diacetate; methanesulfonic acid in acetic acid T=80°C; 0.583333 h;

1: 53 percent / K2CO3, CuO / pyridine / 18 h / Heating 2: 1.01 g / KOH / H2O; dimethylsulfoxide / 3.5 h / Heating 3: 730 mg / copper(II) chromite / quinoline / 4 h / 200 °C 4: 9.7 mg / Pd(OAc)2, methanesulphonic acid / acetic acid / 0.58 h / 80 °C View Scheme

1: 730 mg / copper(II) chromite / quinoline / 4 h / 200 °C 2: 9.7 mg / Pd(OAc)2, methanesulphonic acid / acetic acid / 0.58 h / 80 °C View Scheme

1: 13.0 g / iodine, silver trifluoroacetate / CHCl3 / 0.67 h 2: copper bronze 3: 4.85 g / phosphoryl chloride / 2.75 h / Heating 4: 9.6 g / boron trichloride / CH2Cl2 / 1 h / -10 °C 5: 8.25 g / zinc amalgam, conc. hydrochloric acid / acetic acid; H2O / 2 h / Heating 6: 1.) hydrobromic acid, 2.) potassium carbonate / 1.) glacial acetic acid, reflux, 18 h, 2.) DMF, 24 h View Scheme

1: 4.85 g / phosphoryl chloride / 2.75 h / Heating 2: 9.6 g / boron trichloride / CH2Cl2 / 1 h / -10 °C 3: 8.25 g / zinc amalgam, conc. hydrochloric acid / acetic acid; H2O / 2 h / Heating 4: 1.) hydrobromic acid, 2.) potassium carbonate / 1.) glacial acetic acid, reflux, 18 h, 2.) DMF, 24 h View Scheme

1: copper bronze 2: 4.85 g / phosphoryl chloride / 2.75 h / Heating 3: 9.6 g / boron trichloride / CH2Cl2 / 1 h / -10 °C 4: 8.25 g / zinc amalgam, conc. hydrochloric acid / acetic acid; H2O / 2 h / Heating 5: 1.) hydrobromic acid, 2.) potassium carbonate / 1.) glacial acetic acid, reflux, 18 h, 2.) DMF, 24 h View Scheme

1: 9.6 g / boron trichloride / CH2Cl2 / 1 h / -10 °C 2: 8.25 g / zinc amalgam, conc. hydrochloric acid / acetic acid; H2O / 2 h / Heating 3: 1.) hydrobromic acid, 2.) potassium carbonate / 1.) glacial acetic acid, reflux, 18 h, 2.) DMF, 24 h View Scheme

sodium methylate 1.) reflux, methanol; Yield given. Multistep reaction;

hydrogen bromide; potassium carbonate 1.) glacial acetic acid, reflux, 18 h, 2.) DMF, 24 h; Yield given. Multistep reaction. Yields of byproduct given;