Short-RInChIKey=SA-FUHFF-UHFFFADPSC-BEGUWTIVAN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

4,5-Dibromobenzene-1,2-diamine (400 mg, 1.50 mmol, 1.00 equiv), phenylboronic acid (458 mg, 3.76 mmol, 2.50 equiv) and tetrakis(triphenylphosphine)palladium(0) (69.5 mg, 60.2 μmol, 0.0400 equiv) were put under N2 atmosphere. Then toluene (35.0 mL) and 2 M potassium carbonate (3.12 g, 22.6 mmol, 15.0 equiv) solution in water (10.0 mL) were added. The mixture was stirred at 80 °C for 24 h. The solution was allowed then to reach 21 °C. Ethyl acetate was added (50 mL) and the organic layer was washed with brine (100 mL). Then the aqueous layer was extracted with ethyl acetate (50 mL) x3. The combined organic layers were combined, dried over Na2SO4, and filtered. The solvent was removed under reduced pressure.