Pyridine → 2-(3-Bromophenoxy)isoindoline-1,3-dione

Participants

Reaction Steps

To a mixture of 3-bromophenylboronic acid (246 mg, 1.23 mmol), 2-hydroxyisoindoline-1,3-dione (100 mg, 0.61 mmol), cupric acetate (223 mg, 1.23 mmol) and activated 4 Å molecular sieves (155 mg) in 1,2-dichloroethane (3 mL) under a nitrogen atmosphere was added pyridine (0.11 mL, 1.35 mmol). The reaction was stirred at ambient temperature for 24 h, concentrated in vacuo and purified by flash column chromatography (82:18 hexanes/ethyl acetate) to provide 2-(3-bromophenoxy)isoindoline-1,3-dione (102 mg, 52%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.93 (dd, J=5.4, 3.0 Hz, 2H), 7.83 (dd, J=5.6, 3.0 Hz, 2H), 7.33 (t, J=2.1 Hz, 1H), 7.29 (dt, J=7.8, 2.0 Hz, 1H), 7.22 (t, J=8.1, 1H), 7.16-7.10 (m, 1H).

Provenance & Evidence