Iodoethane → HCID 59636759, Verbindung

HRID 383848

Reaktionsgleichung

Reaktionsgleichung von HRID 383848
[CH2:1](I)[CH3:2].[Br:4][C:5]1[C:13]2[O:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[CH:8]=[C:7]([F:17])[CH:6]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:4][C:5]1[C:13]2[O:12][C:11]([C:14]([O:16][CH2:1][CH3:2])=[O:15])=[CH:10][C:9]=2[CH:8]=[C:7]([F:17])[CH:6]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 179827017-Bromo-5-fluorobenzofuran-2-carboxylic acid

Produkt 1

HCID 59636759HCID 59636759, VerbindungAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Ethyl iodide (4.6 ml, 57.2 mmol) was added to a mixture of 7-bromo-5-fluoro-benzofuran-2-carboxylic acid (3.7 g, 14.3 mmol) and sodium bicarbonate (4.8 g, 57.2 mmol) in anhydrous dimethylformamide (40 mL). The mixture was heated at 55° C. for 18 h, cooled to rt, quenched with water (20 mL) and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1) to give 3.7 g (90%) of the product.

Aufarbeitung

  1. temperaturecooled to rt
  2. customquenched with water (20 mL)
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by flash chromatography (SiO2; hexane/DCM; 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-336d4b8ed6594011bc6c0c7e2af2fd21
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367676B2

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