Ethyl chloroacetate → Ethyl 4-bromobenzofuran-2-carboxylate

HRID 1740298

Reaktionsgleichung

Reaktionsgleichung von HRID 1740298
[Br:1][C:2]1[C:7]([CH:8]=O)=[C:6]([OH:10])[CH:5]=[CH:4][CH:3]=1.Cl[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:7]2[CH:8]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 119547682-Bromo-6-hydroxybenzaldehyde

Produkt 1

HCID 21838105Ethyl 4-bromobenzofuran-2-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 6-bromo-2-hydroxybenzaldehyde (4.48 g), ethyl chloroacetate (3.55 g) and powdered potassium carbonate (6.16 g) in N,N-dimethylformamide (56 ml) was stirred at 120° C. for one hour. Insoluble materials were filtered off and the solvent was removed under reduced pressure. Ethyl acetate and water were added to the residue, and the mixture was acidified by hydrochloric acid solution. The layers were separated and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and toluene (1:1) to afford 4-bromo-2-ethoxycarbonylbenzofuran (4.20 g).

Aufarbeitung

  1. filtrationInsoluble materials were filtered off
  2. customthe solvent was removed under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. customThe layers were separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and toluene (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-98fd762db4624387b28eb07581b62cdc
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968985

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