5-Bromo-2-furanecarboxylic acid → Methyl 5-bromofuran-2-carboxylate

HRID 703510

Reaktionsgleichung

Reaktionsgleichung von HRID 703510
[CH3:1]O.B(F)(F)F.[Br:7][C:8]1[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=1>CO>[Br:7][C:8]1[O:12][C:11]([C:13]([O:15][CH3:1])=[O:14])=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 685115-Bromo-2-furanecarboxylic acidHCID 11062313Boron, trifluoro(methanol)-, (T-4)-2×

Produkt 1

HCID 599633Methyl 5-bromofuran-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Boron trifluoride methanol (6.3 ml, 7.6 g) was added to a stirred solution of 5-bromofuran-2-carboxylic acid (10 g) in methanol (90 ml) and heated under reflux under nitrogen for 5 hours. More boron trifluoride methanol (5 ml) was added and the mixture heated under reflux for 5 hours, allowed to cool to room temperature and stand for 10 hours before the solvent was removed in vacuo and the residue poured into saturated sodium hydrogen carbonate solution (300 ml) and extracted with ethyl acetate (3×200 ml). The extract was washed with saturated sodium hydrogen carbonate solution (2×100 ml), dried over MgSO4, and the solvent removed in vacuo to give methyl 5-bromofuran-2-carboxylate, m.p. 62° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux under nitrogen for 5 hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 5 hours
  5. customwas removed in vacuo
  6. additionthe residue poured into saturated sodium hydrogen carbonate solution (300 ml)
  7. extractionextracted with ethyl acetate (3×200 ml)
  8. washThe extract was washed with saturated sodium hydrogen carbonate solution (2×100 ml)
  9. dry with materialdried over MgSO4
  10. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-347464d7359a4fd8b895aa8d88b094e5
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04983619

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