Trichloroacetonitrile → 2,4-Difluorobenzyl trichloroacetimidate

HRID 2296818

Reaktionsgleichung

Reaktionsgleichung von HRID 2296818
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Cl:11][C:12]([Cl:16])([Cl:15])[C:13]#[N:14]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.[OH-].[K+]>[Cl:11][C:12]([Cl:16])([Cl:15])[C:13](=[NH:14])[O:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1]

Komponenten

6

Edukt 2

HCID 11011TrichloroacetonitrileHCID 918672,4-Difluorobenzyl alcohol

Produkt 1

HCID 110770742,4-Difluorobenzyl trichloroacetimidateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Tetrabutyl ammonium hydrogen sulphate (15 mg) was added to 2,4-difluorobenzylalcohol (1.0 g, 6.94 mmol) in CH2Cl2 (10 ml) and KOH (50%, 10 ml). This mixture was cooled to −15° C. prior to the addition of trichloroacetonitrile (1.2 ml, 8.32 mmol). After 30 min at −15° C. and 3 h at ambient temperature the phases were separated. The aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried with MgSO4 and reduced to one third. The residue was filtered through celite and concentrated to give the crude 2,4-difluorobenzyl trichloroacetimidate (1.83 g, 92%) as a yellow oil.

Aufarbeitung

  1. custom3 h at ambient temperature the phases were separated
  2. extractionThe aqueous phase was extracted twice with CH2Cl2
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. filtrationThe residue was filtered through celite and
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-28cd121bda794ab8b9cb5eef5712f152
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489364B2

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