Boron tribromide → Ethyl 5-hydroxybenzofuran-2-carboxylate

HRID 493168

Reaktionsgleichung

Reaktionsgleichung von HRID 493168
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 5212832-Benzofurancarboxylic acid, 5-methoxy-, ethyl ester

Produkt 1

HCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The above prepared 5-methoxy-benzofuran-2-carboxylic acid ethyl ester (8.10 g, 36.8 mmol) was dissolved in 250 mL of CH2Cl2, cooled to 0° C., and treated with BBr3 (73.6 mL of 1M solution in CH2Cl2, 2 eq.). After 2 h, the reaction mixture was carefully poured onto crashed ice, twofold extracted with CH2Cl2, washed with brine, dried over magnesium sulfate, and evaporated to dryness. Ensuing flash chromatography (SiO2, hexane/AcOEt=8/2) delivered then 5.63 g of the title compound as off-white crystals.

Aufarbeitung

  1. additionthe reaction mixture was carefully poured
  2. extractiontwofold extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fae4dd29020d4c56ba37b03c148f2d48
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534788B2

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