Methyl iodide → Methyl (4-fluorophenyl)methoxyacetate

HRID 1009399

Reaction equation

HRID 1009399 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[F:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]([OH:16])C(O)=O)=[CH:10][CH:9]=1.CI.[C:21]([O:24][CH2:25]C)(=[O:23])[CH3:22]>CN(C=O)C.O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][O:16][CH2:22][C:21]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 980684-Fluoromandelic acid

Product 1

HCID 57267346Methyl (4-fluorophenyl)methoxyacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (6.5 g) was added to a solution of 4-fluoromandelic acid (CAS #395-33-5, 1.7 g) and methyl iodide (1.9 mL) in DMF (15 ml), and the reaction solution was stirred at room temperature for 11 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.22 g of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-402944f252fe46458ff56e44e6e46225
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Linked notes

Loading…