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

HRID 2298266Notes

Reaction equation

HRID 2298266 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.C(=O)([O-])[O-].[Na+].[Na+].[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[F:33]>C1C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:26][C:27]1[CH:28]=[C:29]([C:2]2[C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[O:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH:30]=[CH:31][C:32]=1[F:33]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

Product 1

HCID 98008014-(3-chloro-4-fluorophenyl)-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanoneYield 25%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (112 mg) and tetrakis(triphenylphosphine)palladium(0) (54 mg) in 7 ml benzene and 1 ml ethanol, were added 2 M aqueous sodium carbonate (0.22 ml) and (3-chloro-4-fluorophenyl)boronic acid (82 mg). The reaction solution was kept at reflux for 24 hours. Then the solvent was evaporated off under reduced pressure. The resulting residue was extracted with 50 ml 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 yield 32 mg of 4-(3-chloro-4-fluorophenyl)-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 162-164° C. NMR: δ1.58 (s, 6H), 3.09 (s, 3H), 7.13 (m, 2H), 7.40 (d, J=6.6 Hz, 1H), 7.83 (d, J=8.1 Hz, 2H), 7.97 (d, J=8.1 Hz, 2H). IR (cm−1): 2930, 1700, 1587, 1503, 1404, 1317, 1150, 1068, 913, 771, 744.

Workup

  1. temperatureat reflux for 24 hours
  2. customThen the solvent was evaporated off under reduced pressure
  3. extractionThe resulting residue was extracted with 50 ml water and dichloromethane (50 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resulting residue was separated by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-c5e04b1790be464698d7d6c750636110
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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