Water → Methyl 5-bromo-3-hydroxythiophene-2-carboxylate

HRID 533225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 533225
B(Br)(Br)Br.[CH3:5][O:6][C:7]([C:9]1[S:10][C:11]([Br:16])=[CH:12][C:13]=1[O:14]C)=[O:8].O>C(Cl)Cl>[CH3:5][O:6][C:7]([C:9]1[S:10][C:11]([Br:16])=[CH:12][C:13]=1[OH:14])=[O:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 25134Boron tribromideHCID 59857165Methyl 5-bromo-3-methoxythiophene-2-carboxylate

Produkt 1

HCID 59857018Methyl 5-bromo-3-hydroxythiophene-2-carboxylateAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

BBr3 (26 mL, 1.0 M in heptane, 25.9 mmol, 3.0 Eq.) was added dropwise to a stirred solution of 5-Bromo-3-methoxy-thiophene-2-carboxylic acid methyl ester (2.17 g, 8.62 mmol, 1.0 Eq.) in anhydrous DCM (100 mL) at −10° C. under nitrogen. After 1.5 hours, water (40 mL) was added and the aqueous layer extracted with DCM (3×20 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (50% Petroleum ether/DCM) to give the sub-title compound as a white solid (1.67 g, 7.04 mmol, 81%); 1H NMR (400 MHz, CDCl3) δ 3.90 (3H, s), 6.80 (1H, s), 9.68 (1H, br s).

Aufarbeitung

  1. extractionthe aqueous layer extracted with DCM (3×20 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (50% Petroleum ether/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-98c263cbcf12446fb3f3bd9305c26698
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853244B2

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