Methyl iodide → HCID 11063072, compound

HRID 2252022Notes

Reaction equation

HRID 2252022 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[CH:20]=[CH:19][C:13]([CH:14]([OH:18])[C:15]([OH:17])=[O:16])=[CH:12][CH:11]=1>CN(C)C=O.O.C(OCC)(=O)C>[F:9][C:10]1[CH:20]=[CH:19][C:13]([CH:14]([OH:18])[C:15]([O:17][CH3:1])=[O:16])=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 980684-Fluoromandelic acid

Product 1

HCID 11063072HCID 11063072, compoundYield 87.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add potassium carbonate (12 g, 87 mmol) followed by iodomethane (7.37 mL, 118 mmol) to a 0° C. solution of p-fluoromandelic acid (79 mmol, 13.4 g) in 160 mL dry dimethylformamide under a nitrogen atmosphere. Stir the resulting mixture at 0° C. for 1 hour and at room temperature over night. Pour the reaction mixture over ice, dilute with water and ethyl acetate, and extract the aqueous layer three times with ethyl acetate. Wash the combined organic layers with cold water and saturated aqueous sodium chloride, dry over sodium sulfate and concentrate under reduced pressure to provide 12.7 g (87%) of the desired compound as a light yellow oil.

Workup

  1. waitat room temperature over night
  2. additionPour the reaction mixture over ice
  3. extractionextract the aqueous layer three times with ethyl acetate
  4. washWash the combined organic layers with cold water and saturated aqueous sodium chloride
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-087a8e67c49a460ba80f0bc28fe6d753
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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