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Methyl morpholine oxide → 5-Fluorobenzofuran-4-carbaldehyde

HRID 1602401
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1602401
C[N+]1([O-])CC[O:5]CC1.Br[CH2:10][C:11]1[C:16]2[CH:17]=[CH:18][O:19][C:15]=2[CH:14]=[CH:13][C:12]=1[F:20].BrCC1C(F)=CC2C=COC=2C=1>C(#N)C>[F:20][C:12]1[C:11]([CH:10]=[O:5])=[C:16]2[CH:17]=[CH:18][O:19][C:15]2=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 82029Methyl morpholine oxideHCID 196116346-Bromomethyl-5-fluorobenzofuranHCID 196116884-Bromomethyl-5-fluorobenzofuran

Produkt 1

HCID 196116515-Fluorobenzofuran-4-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of the N-methylmorpholine-N-oxide (13.6 g) in acetonitrile (135 ml) containing 3 Å molecular sieves (13.2 g) was stirred at room temperature overnight and cooled in ice. A solution of 4-bromomethyl-5-fluorobenzofuran and 6-bromomethyl-5-fluorobenzofuran (13.33 g) in acetonitrile (35 ml) was added and the mixture stirred at 5° for 4 h. The mixture was filtered and the filtrate evaporated to dryness. Water and ethyl acetate were added to the residue and the organic phase separated, dried and evaporated to give the mixture of aldehydes. The mixture was separated by chromatography on silica (600 g) using a mixture of ethyl acetate and hexane (1:9) as the eluant to give the title compound (A) (2.19 g);

Aufarbeitung

  1. temperaturecooled in ice
  2. stirringthe mixture stirred at 5° for 4 h
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to dryness
  5. additionWater and ethyl acetate were added to the residue
  6. customthe organic phase separated
  7. customdried
  8. customevaporated
  9. customto give
  10. customThe mixture was separated by chromatography on silica (600 g)
  11. additiona mixture of ethyl acetate and hexane (1:9) as the eluant

Quellen und Nachweise

ORD-Eintrag
ord-ba45fbecad2a46558d417bd4898ff938
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05981572

Notizen zur Reaktion

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