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Hydrochloric Acid → 5-(1,1-Difluoroethyl)-2-(trifluoromethoxy)benzaldehyde

HRID 1634328
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1634328
[F:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([O:13][C:14]([F:17])([F:16])[F:15])=[C:9]([CH:12]=1)[C:10]#N)([F:4])[CH3:3].[OH2:18].Cl>C(Cl)Cl>[F:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([O:13][C:14]([F:17])([F:16])[F:15])=[C:9]([CH:12]=1)[CH:10]=[O:18])([F:4])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 186776385-(1,1-Difluoroethyl)-2-(trifluoromethoxy)benzonitrile

Produkt 1

HCID 186776085-(1,1-Difluoroethyl)-2-(trifluoromethoxy)benzaldehydeAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of Compound 24 (1.31 g, 5.22 mmol) in dry CH2Cl2(20 ml) was added a solution of diisobutylaluminum hydride(DIBAL) (6.20 ml, 6.26 mmol, 1.01M in toluene solution) with ice-cooling. The reaction mixture was stirred at 0° C. for 3 h. To the mixture was added H2O(6 ml), followed by 6M HCl aq. (20 ml) and stirred at room temperature for 1.5 h. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with sat. NaHCO3 aq. and brine, dried(MgSO4) and concentrated in vacuo to give crude product. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (50:1-30:1) to give Compound 25 (1.17 g, 88%) as a yellow oil.

Aufarbeitung

  1. temperaturecooling
  2. stirringstirred at room temperature for 1.5 h
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined solution was washed with sat. NaHCO3 aq. and brine, dried(MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give crude product
  8. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate (50:1-30:1)

Quellen und Nachweise

ORD-Eintrag
ord-e29c891a480e4fba8bc68dfae4669c79
Quelldatensatz
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06506775B1

Notizen zur Reaktion

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