Water → Methyl 4-bromofuran-2-carboxylate

HRID 1845536

Reaktionsgleichung

Reaktionsgleichung von HRID 1845536
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.C([Mg]Cl)(C)C.O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 12239443Methyl 4-bromofuran-2-carboxylateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of methyl 4,5-dibromo-2-furancarboxylate (3.3 g, 11.62 mmol) in tetrahydrofuran (46 ml) at −40° C. was added isopropylmagnesium chloride (6.97 ml, 13.95 mmol). After 1 h, Water (11 ml) was added and the solution warmed to 25° C. The reaction mixture was then partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (3% EtOAc in hexanes) affording methyl 4-bromo-2-furancarboxylate (1.4 g, 6.49 mmol, 56% yield) as a yellow solid: LCMS (ES) m/e 205, 207 (M, M+2)+.

Aufarbeitung

  1. customThe reaction mixture was then partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (3% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7e41a5f653124869b57e1a3f1590c6c3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946278B2

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