Ethyl bromoacetate → HCID 68667949, compound

Participants

Reaction Steps

A mixture of 1-[2-fluoro-4-(5-fluoropyridin-2-yl)phenyl]ethanone (3.6 g, 15.3 mmol) and ethyl bromoacetate (12.8 g, 76.5 mmol) in tetrahydrofuran (35 mL) was added dropwise to a refluxing suspension of zinc (Reike, activated) (5 g) in tetrahydrofuran (100 mL). After stirring at reflux for a further 15 min, the reaction was cooled, poured into ice water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 10-50% ethyl acetate/hexane over 48 fractions afforded ethyl 3-[2-fluoro-4-(5-fluoropyridin-2-yl)phenyl]-3-hydroxybutanoate.

Provenance & Evidence