Methyl iodide → Methyl 2-(4-Fluorophenyl)-2-hydroxyacetate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence