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

HRID 2298267Notes

Reaction equation

HRID 2298267 reaction equation
Br[C:2]1[C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:55][O:56][C:57]1[CH:62]=[CH:61][C:60](B(O)O)=[CH:59][CH:58]=1>C1C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][C:4]1([CH3:18])[C:3](=[O:19])[C:2]([C:60]2[CH:61]=[CH:62][C:57]([O:56][CH3:55])=[CH:58][CH:59]=2)=[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[O:5]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 201262(4-Methoxyphenyl)boronic acidHCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

Product 1

HCID 183855972,2-dimethyl-4-(4-methoxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanoneYield 24.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 241BenzeneSolvent

Procedure

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (220 mg), 1,3-bis(diphenylphosphino)propane (24 mg) and palladium(II) acetate (6.1 mg) in 30 ml benzene, were added 2 M aqueous sodium carbonate (0.22 ml) and 4-methoxybenzeneboronic acid (90 mg). The reaction solution was kept at reflux for 24 hours. Then the solvent was removed under reduced pressure. The resulting residue was purified by a procedure similar to the purification method in Example 2 to yield 55 mg of 2,2-dimethyl-4-(4-methoxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. NMR: δ1.56 (s, 6H), 3.07 (s, 3H), 3.83 (s, 3H), 6.92 (d, J=8.7 Hz, 2H), 7.23 (d, J=9.0 Hz, 2H), 7.89(dd, J=8.7, 8.7 Hz, 4H). IR (cm−1): 2925, 1697, 1592, 1149, 1031, 912, 745.

Workup

  1. temperatureat reflux for 24 hours
  2. customThen the solvent was removed under reduced pressure
  3. customThe resulting residue was purified by a procedure similar to the purification method in Example 2

Sources & evidence

ORD record
ord-b39a03c1f0ff4ef19b93b3829548ddcd
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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