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Triethylamine → E-5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]benzaldehyde

HRID 1672630
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1672630
Br[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:10][C:7]1[CH:8]=[CH:9][C:2](/[CH:18]=[CH:17]/[C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[C:3]([CH:6]=1)[CH:4]=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 125074-MethoxystyreneHCID 80271Tri-o-tolylphosphineHCID 27733212-Bromo-5-fluorobenzaldehyde

Produkt 1

HCID 57831341E-5-Fluoro-2-[2-(4-methoxyphenyl)vinyl]benzaldehydeAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 10 g (49.26 mmol) of 2-bromo-5-fluorobenzaldehyde in 200 ml of dry DMF is mixed with 7.27 g (54.18 mmol) of 4-methoxystyrene, 1.5 g (4.93 mmol) of tri-2-tolylphosphine, 330 mg (1.48 mmol) of palladium(II) acetate and 10.3 ml (73.89 mmol) of triethylamine under argon and stirred at 100° C. for 12 hours. After reaction is complete, the reaction solution is cooled to room temperature and concentrated to dryness. The resulting residue is taken up in 100 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases are dried over sodium sulfate. After filtration, the solution is concentrated to dryness, and the residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 7.79 g (55% yield) of a colorless solid are obtained.

Aufarbeitung

  1. customAfter reaction
  2. temperaturethe reaction solution is cooled to room temperature
  3. concentrationconcentrated to dryness
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe solution is concentrated to dryness
  8. customthe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-b7534bb800864722a5100566d95dfcbb
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07998988B2

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