3-Nitrophenylboronic Acid → HCID 18385616, compound

HRID 2298272Notes

Reaction equation

HRID 2298272 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+].[N+:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)([O-:28])=[O:27]>C1(C)C=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>[CH3:17][C:4]1([CH3:18])[C:3](=[O:19])[C:2]([C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([N+:26]([O-:28])=[O:27])[CH:34]=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 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

Product 1

HCID 18385616HCID 18385616, compoundYield 52.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-eda5640367f248bf80c44b0711ba6e58
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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