Ethyl bromoacetate → ethyl 2-(4-formyl-2-nitrophenoxy)acetate

HRID 1271678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1271678
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[CH3:19]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehyde

Produkt 1

HCID 5305379ethyl 2-(4-formyl-2-nitrophenoxy)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 4-hydroxy-3-nitro-benzaldehyde (6.9 g) and ethyl bromoacetate (5.0 ml) in dimethylformamide (250 ml) was treated with anhydrous potassium carbonate (10 g) and the mixture was heated at 60° C. for 18 hours and evaporated to dryness. The residue was partitioned between water and ether, and the ether layer was washed with 0.5M sodium hydroxide, dried over anhydrous sodium sulphate and evaporated to give an oil that was chromatographed on silica gel (ethyl acetate/dichloromethane) to afford an oil (1.9 g)

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and ether
  3. washthe ether layer was washed with 0.5M sodium hydroxide
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated
  6. customto give an oil that
  7. customwas chromatographed on silica gel (ethyl acetate/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-e9fa6cc2bdd7468d91bb4821e6668ea7
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07205408B2

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