Chloroacetone → HCID 22144837, compound

HRID 1824919Notes

Reaction equation

HRID 1824919 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].Cl[CH2:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.[I-].[K+]>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:11][C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 22144837HCID 22144837, compoundYield 109.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.9 gm (10 mMol) 2-bromo-4-fluorophenol, 0.92 gm (10 mMol) chloroacetone, 0.1 gm potassium iodide, and 1.4 gm (10 mMol) potassium carbonate in 100 mL tetrahydrofuran was heated at reflux for 4 hours. The mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane and 1 N sodium hydroxide. The phases were separated and the aqueous phase extracted well with dichloromethane. The organic phases were combined, washed with 1 N sodium hydroxide, dried over sodium sulfate and concentrated under reduced pressure. The residual was subjected to silica gel chromatography, eluting with hexane containing 20% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 2.7 gm (100%) of the desired compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between dichloromethane and 1 N sodium hydroxide
  5. customThe phases were separated
  6. extractionthe aqueous phase extracted well with dichloromethane
  7. washwashed with 1 N sodium hydroxide
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washeluting with hexane containing 20% ethyl acetate
  11. additionFractions containing product
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-446d4014aa4d47d6ab8f392081c25618
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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