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3-Bromothiophene-2-carboxaldehyde → 3-(Pyridine-2-sulfonyl)thiophene-2-carbaldehyde

HRID 1944462
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944462
[Na+].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O-:10])=[O:9].Br[C:12]1[CH:16]=[CH:15][S:14][C:13]=1[CH:17]=[O:18]>CS(C)=O>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1[CH:17]=[O:18])(=[O:10])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 27970793-Bromothiophene-2-carboxaldehydeHCID 23678794Sodium Pyridine-2-sulfinate

Produkt 1

HCID 866521883-(Pyridine-2-sulfonyl)thiophene-2-carbaldehydeAusbeute 6,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of pyridine-2-sulfinate sodium salt (8.5 g), 3-bromothiophene-2-carbaldehyde (6.5 g) and dimethyl sulfoxide (50 mL) (split equally into four microwave vials) was heated by microwave irradiation at 125° C. for 45 minutes. The combined mixtures were diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume) to afford the title compound as a yellow solid (0.55 g).

Aufarbeitung

  1. customsplit equally into four microwave vials)
  2. additionThe combined mixtures were diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-d9748e056adf4ca4a7766893eebf3c61
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394836B2

Notizen zur Reaktion

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