Sodium Carbonate → Ethyl 5-bromo-4-(3-chlorophenyl)furan-2-carboxylate

HRID 2190123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190123
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[O:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Br:18]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:18][C:12]1[O:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 58064785Ethyl 4-(3-chlorophenyl)furan-2-carboxylate

Produkt 1

HCID 58064768Ethyl 5-bromo-4-(3-chlorophenyl)furan-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

0.82 g (3.27 mmol) of the compound from Example 9A are provided in 21 ml of acetic acid, 0.17 ml (3.27 mmol) of bromine are added and the mixture is stirred at 60° C. overnight. A saturated aqueous sodium carbonate solution is added carefully, and the mixture is extracted with ethyl acetate. The organic phase is washed twice with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 40:1). 1.05 g (91% of theory) of the title compound are obtained.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 40:1)

Quellen und Nachweise

ORD-Eintrag
ord-1a83798df0a747d88e9372c772f53b1f
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324268B2

Notizen zur Reaktion

Wird geladen…