Sodium Carbonate → 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-{4-(trifluoromethoxy)phenyl}-3(2H)-furanone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (150 mg) in 15 ml toluene and 5 ml ethanol, were added 30 mg of tetrakis(triphenylphosphine)palladium(0), 5 ml of saturated aqueous sodium carbonate, and 100 mg of 4-(trifluoromethoxy)benzeneboronic acid. The reaction solution was stirred at 90° C. for 24 hours. Then the solvent was removed under reduced pressure. The resulting residue was extracted with water and dichloromethane. The organic layer was concentrated in vacuo and the resulting residue was separated by column chromatography (hexane/ethylacetate) to yield 60 mg of 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-{4-(trifluoromethoxy)phenyl}-3(2H)-furanone as a solid. mp: 118-120° C. NMR: δ1.58 (s, 6H), 3.08 (s, 3H), 7.20-7.26 (m, 2H), 7.31-7.34 (m, 2H), 7.82-7.85 (m, 2H), 7.95-7.98 (m, 2H). IR (cm−1): 2931, 1698, 1510, 1387, 1258, 1150, 960, 846, 770.

Provenance & Evidence