3-Nitrophenylboronic Acid → HCID 18385616, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (170 mg) in 30 ml toluene and 10 ml ethanol, were added 25 mg of tetrakis(triphenylphosphine)palladium(0), 10 ml of saturated aqueous sodium carbonate, and 120 mg of 3-nitrobenzeneboronic acid. The reaction solution was stirred at 90° C. for 12 hours. Then the solvent was removed under reduced pressure. The resulting residue was extracted with water and dichloromethane (50 ml×3). The organic layer was concentrated in vacuo and the resulting residue was separated by column chromatography (hexane/ethylacetate) to afford 100 mg of 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-(3-nitrophenyl)-3(2H)-furanone as a solid. mp: 158-159° C. NMR: δ1.61 (s, 6H), 3.09 (s, 3H), 7.57 (t, J=7.8 Hz, 1H), 7.64 (m, 1 H), 7.81 (d, J=9.0 Hz, 2H), 7.98 (d, J=8.7 Hz, 2H), 8.19 (m, 2H). IR (cm−1): 2982, 1697, 1529, 1403, 1349, 1150, 959, 770.

Provenance & Evidence