Cesium carbonate → (4-Nitro-2,6-difluoro-phenoxy)-acetic acid methyl ester

HRID 1004079Notes

Reaction equation

HRID 1004079 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([OH:11])=[C:6]([F:12])[CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>>[CH3:24][O:23][C:21](=[O:22])[CH2:20][O:11][C:7]1[C:6]([F:12])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]=1[F:10]

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 6002102,6-Difluoro-4-nitrophenol

Product 1

HCID 54234870(4-Nitro-2,6-difluoro-phenoxy)-acetic acid methyl esterYield 85.2%

Procedure

A mixture of 4-nitro-2,6-difluoro-phenol (5.08 g, 29.0 mmol) and cesium carbonate (10.3 g, 31.7 mmol) in 100 mL acetonitrite was treated with methyl bromoacetate (3.0 mL, 31.7 mmol). The mixture was heated at reflux for 2 h. The mixture was allowed to cool to ambient temperature, and partitioned between water and ethyl acetate. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated to afford material which was purified by silica gel chromatography eluting with hexane: ethyl acetate (2:1). Concentration of the relevant fractions afforded the title compound (6.11 g) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. custompartitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford material which
  9. customwas purified by silica gel chromatography
  10. washeluting with hexane: ethyl acetate (2:1)

Sources & evidence

ORD record
ord-51a96cd0c4364e8db46d541fd04a825e
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

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