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N-Formylmorpholine → 6-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde

HRID 1772868
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1772868
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([Si:14]([CH3:17])([CH3:16])[CH3:15])=[C:9]([F:18])[CH:8]=1.[CH:19](N1CCOCC1)=[O:20]>C1COCC1>[Cl:6][C:7]1[C:8]([CH:19]=[O:20])=[C:9]([F:18])[C:10]([Si:14]([CH3:15])([CH3:17])[CH3:16])=[C:11]([F:13])[CH:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 20417N-FormylmorpholineHCID 18935733(4-Chloro-2,6-difluorophenyl)trimethylsilaneHCID 178418339Butyllithium

Produkt 1

HCID 866138416-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehydeAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A solution of 2.5M n-BuLi in hexanes (60 ml, 0.15 mol) was added drop-wise to a solution of (4-chloro-2,6-difluorophenyl)trimethylsilane (assumed 0.13 mol) in THF (180 mL) cooled to −70° C. under Ar. After the addition was complete, the mixture was stirred for 1 h before a solution of N-formylmorpholine (20 mL, 0.2 mol) in THF (25 mL) was added dropwise. The reaction was allowed to warm to rt with stirring and then cooled to 0° C. and quenched with H2O. Ether was added, the phases were separated, the aqueous phase was re-extracted with ether and the combined organics washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (35 g) as an orange oil which was used without further purification.

Aufarbeitung

  1. additionAfter the addition
  2. additionwas added dropwise
  3. temperatureto warm to rt
  4. temperaturecooled to 0° C.
  5. customquenched with H2O
  6. additionEther was added
  7. customthe phases were separated
  8. extractionthe aqueous phase was re-extracted with ether
  9. washthe combined organics washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8cd4521317aa40ea96bc54194ef87c60
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249160B2

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