Sodium Carbonate → Ethyl 5-bromofuran-3-carboxylate

HRID 537060

Reaktionsgleichung

Reaktionsgleichung von HRID 537060
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:2]1.[Br:11]Br.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:11][C:5]1[O:1][CH:2]=[C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 69201Ethyl 3-furoate

Produkt 1

HCID 14592142Ethyl 5-bromofuran-3-carboxylateAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 3-furoate (50.0 g, 360 mmol) in chloroform (380 mL) was added bromine (56.0 g, 360 mmol) in chloroform. The reaction mixture was allowed to stir at rt overnight and then poured into 10% aqueous Na2CO3. The mixture was extracted with DCM. The organic solutions were combined and washed with water until pH=7. The organic solution was concentrated and then distilled to give ethyl 5-bromo-3-furoate (42 g, 40%).

Aufarbeitung

  1. extractionThe mixture was extracted with DCM
  2. washwashed with water until pH=7
  3. concentrationThe organic solution was concentrated
  4. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-7406ec14cb494712806516432f970ee3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859768B2

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