Benzyl Bromide → 4-Benzyloxyphenylacetic acid ethyl ester

HRID 524408

Reaktionsgleichung

Reaktionsgleichung von HRID 524408
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16]>C(#N)C>[CH2:7]([O:4][C:1]1[CH:12]=[CH:13][C:8]([CH2:16][C:15]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:10]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 10796Cesium carbonate

Produkt 1

HCID 27374284-Benzyloxyphenylacetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of ethyl-4-hydroxy phenyl acetate (10 g, 55.49 mmol) in 50 mL of dry acetonitrile was added in a drop wise manner to a suspension of cesium carbonate (36 g, 110.98 mmol) in 50 mL of dry acetonitrile. Reaction mixture was allowed to stir at rt for 10 min then benzyl bromide (7.25 mL, 61.03 mmol) was added drop wise and continued to stir overnight at rt. Reaction was quenched with water and solid was filtered through Buchner funnel, filtrate obtained was diluted with ethyl acetate, and organic layer was washed with water, brine and dried over anhydrous sodium sulphate. Solvent was removed under reduced pressure to obtain crude product which was purified using column chromatography using 5-10% ethyl acetate in hexane to afford 8.0 g of liquid.

Aufarbeitung

  1. customReaction mixture
  2. stirringcontinued to stir overnight at rt
  3. customReaction
  4. customwas quenched with water and solid
  5. filtrationwas filtered through Buchner funnel, filtrate
  6. customobtained
  7. washwas washed with water, brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. customSolvent was removed under reduced pressure
  10. customto obtain crude product which
  11. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-9b3ff5f2fe59417a9b17a840ed433764
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340506B2

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