3,4-Dihydroxybenzaldehyde → 4-(Difluoromethoxy)-3-hydroxybenzaldehyde

HRID 3021

Reaktionsgleichung

Reaktionsgleichung von HRID 3021
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Cl[C:12]([F:18])([F:17])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:17][CH:12]([F:18])[O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[OH:1]

Komponenten

5

Edukt 3

HCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetate

Produkt 1

HCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehydeAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3,4-Dihydroxybenzaldehyde (0.50 g, 3.62 mmol, Aldrich), methyl chlorodifluoroacetate (0.52 g, 3.62 mmol, Aldrich) and potassium carbonate (0.50 g, 3.62 mmol) were combined in DMF (5.0 mL) under an argon atmosphere. After stirring at 60°-65° C. for 3 h, DMF was removed in vacuo and the residue was partioned between aqueous 3N HCl and ether. The aqueous layer was extracted three times with ether. The combined organic extracts were washed with water, with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide the title compound as a white solid (0.20 g, 38%). mp 83°-85° C.

Aufarbeitung

  1. customDMF was removed in vacuo
  2. extractionThe aqueous layer was extracted three times with ether
  3. washThe combined organic extracts were washed with water, with brine
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e57e5ba30ba5446d9ef33fda5e7bc0ab
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731477

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