[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([F:3])[CH:5]=1)[CH3:17]A 50 ml three-necked round-bottomed flask equipped with temperature probe and nitrogen bubbler was charged with Sodium Hydride (785 mg, 19.6 mmol) and DMF (10.0 ml) and cooled to 0° C. A solution of 3-Fluorophenol (2.00 g, 17.8 mmol) in DMF (2.0 ml) was added dropwise maintaining reaction temperature below 10° C. The mixture was stirred for an additional 15 minutes then Ethyl bromoacetate (2.48 ml, 22.3 mmol) was added dropwise maintaining the reaction temperature below 10° C. The reaction was stirred at room temperature for 4 hours. The reaction was then concentrated under reduced pressure and the crude product was taken up in Ethyl acetate, washed with water, dried (Na2SO4), filtered, concentrated and further purified via flash chromatography using 4:1/heptane:Ethyl acetate as eluant. Fractions containing product were combined and concentrated to afford (3-Fluoro-phenoxy)-acetic acid ethyl ester (2.26 g, 69%) as a clear oil.
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