Ethyl bromoacetate → Ethyl (2-bromo-3-formylphenoxy)acetate

HRID 561836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561836
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[Br:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 37146742-Bromo-3-hydroxybenzaldehyde

Produkt 1

HCID 59515317Ethyl (2-bromo-3-formylphenoxy)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-3-hydroxybenzaldehyde (1 eq.) in DMF (0.4 M) was added cesium carbonate (1.2 eq.) and ethyl bromoacetate (1 eq.). The resulting suspension was stirred at RT for 16 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic extracts were washed with water and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a red oil. Purification by way of column chromatography (SiO2, 5:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) afforded the title compound.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo
  5. customafforded the crude product as a red oil
  6. customPurification by way of column chromatography (SiO2, 5:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-05babb2afc18419a9894d817c93427e8
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063105B2

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