Water → HCID 19261280, compound

HRID 1697759Notes

Reaction equation

HRID 1697759 reaction equation
[F-].[Cs+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH:12]1[CH2:16][CH2:15][O:14][C:13]1=[O:17].O>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 25953Cesium fluorideHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 19261280HCID 19261280, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Cesium fluoride (7.6 g) was added to a solution of 4-chlorophenol (1.29 g) in dimethylformamide (35 mL) and the mixture was stirred at 100° C. for 5 min. 3-bromodihydrofuran-2(3H)-one (3.3 g) was added and the reaction mixture was heated to 120° C. for 1.5 h. The reaction mixture was poured into water and extracted with EtOAc. The aqueous layer was extracted with ethylacetate. The organic layers were washed with water, dried over sodium sulfate and filtered. The crude mixture was concentrated to dryness and purified by chromatography on silica gel to yield the title compound as a colorless oil (1.17 g; 55%). MS (ESI): m/z=212 [M]+.

Workup

  1. temperaturethe reaction mixture was heated to 120° C. for 1.5 h
  2. extractionextracted with EtOAc
  3. extractionThe aqueous layer was extracted with ethylacetate
  4. washThe organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe crude mixture was concentrated to dryness
  8. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-c47b9862a2944effa27b5175729b2586
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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