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Hydrochloric Acid → HCID 12097219, Verbindung

HRID 1464600
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464600
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12][Si:13]([CH2:16][Mg]Cl)([CH3:15])[CH3:14].Cl>C(OCC)C>[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)([OH:4])[CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1202482-Chloro-4'-fluoroacetophenoneHCID 178418680HCID 178418680, Verbindung

Produkt 1

HCID 12097219HCID 12097219, VerbindungAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

8.63 g (0.05 mole) of 2-chloro-4'-fluoroacetophenone were dissolved in 60 ml of diethyl ether. The solution was stirred under a stream of nitrogen, and 200 ml (0.057 mole) of a diethyl ether solution of trimethylsilylmethylmagnesium chloride were added dropwise at such a rate that the temperature of the reaction mixture did not rise above 15° C.-20° C. The reaction mixture was then stirred for a further 1 hour at room temperature, after which it was poured into 200 ml of ice water, and its pH was adjusted to a value of 6-7 by the addition of 5% w/v aqueous hydrochloric acid. It was then extracted with 100 ml of ethyl acetate. The organic extract was washed twice, each time with 50 ml of a saturated aqueous solution of sodium chloride It was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to afford a crude oily product. This crude oily product was purified by silica gel column chromatography, using mixtures of ethyl acetate and hexane ranging from 1:10 to 1:5 by volume, to give 8.8 g (yield 67.7%) of the title compound as an oily substance.

Aufarbeitung

  1. additionwere added dropwise at such a rate that the temperature of the reaction mixture
  2. customdid not rise above 15° C.-20° C
  3. additionwas adjusted to a value of 6-7 by the addition of 5%
  4. extractionIt was then extracted with 100 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed twice
  7. dry with materialeach time with 50 ml of a saturated aqueous solution of sodium chloride It was then dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customto afford a crude oily product
  10. customThis crude oily product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0746a5345041433a8ae27610ef50f37a
Quelldatensatz
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05306712

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