Ethyl bromoacetate → HCID 68667949, compound

HRID 216375Notes

Reaction equation

HRID 216375 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15](=[O:17])[CH3:16].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>O1CCCC1.[Zn]>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:15]([OH:17])([CH3:16])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 2

HCID 7748Ethyl bromoacetateHCID 59161947Ethanone, 1-[2-fluoro-4-(5-fluoro-2-pyridinyl)phenyl]-

Product 1

HCID 68667949HCID 68667949, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. temperatureat reflux for a further 15 min
  2. temperaturethe reaction was cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae3339b737c6424cb88cdcab84016b74
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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