Methyl 4,5-Dibromo-2-furancarboxylate → Methyl 4-bromo-5-methylfuran-2-carboxylate

HRID 1845697

Reaktionsgleichung

Reaktionsgleichung von HRID 1845697
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.Cl[Zn][CH3:14]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:14]

Komponenten

5

Edukt 2

HCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178477798HCID 178477798, Verbindung

Produkt 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4,5-dibromo-2-furancarboxylate (4.5 g, 15.85 mmol) and BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) CHLORIDE (0.38 g, 0.541 mmol) in THF (100 mL) at RT was added chloro(methyl)zinc (15 mL, 30 mmol) dropwise. After stirring for 10 h, the reaction was quenched with NH4Cl (sat'd) (50 mL). The mixture was extracted with EtOAc (50 mL×3), and the collected organic layers were dried over MgSO4. Solvent was removed under vacuum and the resulting residue was purified via column chromatography (silica, EtOAc/Hex 10-20%) to give the title compound (2.5 g, 72%) as a white solid: LC-MS (ES) m/z 220 (M+H)+.

Aufarbeitung

  1. customthe reaction was quenched with NH4Cl (sat'd) (50 mL)
  2. extractionThe mixture was extracted with EtOAc (50 mL×3)
  3. dry with materialthe collected organic layers were dried over MgSO4
  4. customSolvent was removed under vacuum
  5. customthe resulting residue was purified via column chromatography (silica, EtOAc/Hex 10-20%)

Quellen und Nachweise

ORD-Eintrag
ord-0cf7215562f1448a868bae8bfbfd8b32
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946278B2

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