2,6-Dibromoaniline (6.02 g, 24 mmol) and Pd(PPh3)4 (3.88 g, 3.00 mmol) were dissolved in toluene (240 ml). Phenyl boronic acid (8.80 g, 72 mmol) in EtOH (50 ml) was added. Na2CO3 (13 g, 144 mmol) in H2O (70 ml) was added. The reaction mixture was reflux for 24 hrs. The organic layer was thin separated and the amine precipitated as hydrochloride salt by addition of 20 ml of HCl. The precipitate was isolated. The salt was suspended in ether, and 2 M Na2CO3 was added. The organic layer was dried over Na2SO4 and the solvent was evaporated. The yield was 90%. 1H NMR (CDCl3): δ 7.44 (t, 4H, Harom), 7.39 (t, 4H, Harom), 7.29 (d, 2H, Harom), 7.07 (d, 2H, Harom), 6.82 (t, 1H, Harom), 3.77 (s, 2H, NH2).
