Potassium phthalamide → 2-{[3-Bromo-2-(methyloxy)phenyl]methyl}-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3-(bromomethyl)-2-(methyloxy)benzene (41.4 g, 0.15 mol) in DMF (350 mL), Potassium Phthalamide (PhtK) (28.8 g, 0.16 mol) was added, and the mixture was heated to 90° C. over night. Then the solvent was removed under reduced pressure. The residue was dissolved in CHCl3 (300 mL), and filtered. The filtrate was washed with H2O (100 mL×2), brine (100 mL), and dried over Na2SO4. After removing the solvent, the residue was recrystallized with EtOH (200 mL). 26.7 g of the product was obtained as white solid. Yield: 52.1%. 1H NMR (400 MHz, CDCl3) δ 3.98 (s, 3 H), 4.95 (s, 2H), 6.93 (t, J=8.0 Hz, 1 H), 7.20 (d, J=0.8 Hz, 1 H), 7.45 (d, J=8.0 Hz, 1 H), 7.72-7.87 (m, 4 H).

Provenance & Evidence