Boron tribromide → Ethyl 6-hydroxybenzofuran-3-carboxylate

HRID 250273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250273
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 45489697Ethyl 6-methoxybenzofuran-3-carboxylate

Produkt 1

HCID 59152646Ethyl 6-hydroxybenzofuran-3-carboxylateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A −78° C. solution of 6-methoxy-benzofuran-3-carboxylic acid ethyl ester (1.50 g, 6.81 mmol) in dichloromethane (20 mL) is treated with boron tribromide (20 mL) dropwise. The mixture is stirred at 0° C. for 60 minutes. The reaction is quenched by adding MeOH (10 mL) dropwise over 10 minutes. The mixture is concentrated. The residue is purified via flash chromatography eluting with 25% EtOAc/hexanes to provide the title compound (0.95 g, 68%). ES/MS m/e 207.0 (M+1), 205.0 (M−1).

Aufarbeitung

  1. customThe reaction is quenched
  2. additionby adding MeOH (10 mL) dropwise over 10 minutes
  3. concentrationThe mixture is concentrated
  4. customThe residue is purified via flash chromatography
  5. washeluting with 25% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8b21c22bbc2d46c2bf3a1ead6bbc9c07
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

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