p-Xylyl bromide → 5-Methoxy-2-(4-methylbenzyl)-2,3-dihydroisoindol-1-one

Participants

Reaction Conditions

Reaction Steps

5-Methoxy-2,3-dihydroisoindol-1-one (40 mg, 0.25 mmol), Cs2CO3 (239 mg, 0.74 mmol), 1-bromomethyl-4-methylbenzene (68 mg, 0.37 mmol) in acetonitrile (4 mL) was allowed to stir at room temperature for 18 hours and at 70° C. for 4 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified by column chromatography (30% EtOAc/Hexanes) to afford a white solid (15 mg). 1H NMR (300 MHz, CDCl3): δ 7.81 (d, 1H), 7.18 (q, 4H), 7.00 (dd, 1H), 6.87 (s, 1H), 4.75 (s, 2H), 4.21 (s, 2H), 3.87 (s, 3H), 2.34 (S, 3H).

Provenance & Evidence