1,3-Difluoro-5-nitrobenzene → HCID 9887211, Verbindung

HRID 1901760

Reaktionsgleichung

Reaktionsgleichung von HRID 1901760
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[CH:9]=2)[C:4](=[O:17])[O:3]1.CC(C)([O-])C.[K+].[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[C:30]([F:32])[CH:31]=1>CN(C)C=O>[F:25][C:26]1[CH:27]=[C:28]([N+:33]([O-:35])=[O:34])[CH:29]=[C:30]([F:32])[C:31]=1[CH:11]([N:12]1[CH:16]=[N:15][CH:14]=[N:13]1)[C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:17])[O:3][C:2]2([CH3:18])[CH3:1]

Komponenten

5

Edukt 3

HCID 752721,3-Difluoro-5-nitrobenzeneHCID 233686093,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one2×HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 9887211HCID 9887211, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one (4.47 g Intermediate 1) in N,N-dimethylformamide (250 ml) at 0° under nitrogen was added potassium tert-butoxide (4.53 g). After one hour 3,5-difluoronitrobenzene (3.22 g) was added and stirring continued for five hours. The reaction mixture was partitioned between water and ethyl acetate and the phases separated. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed with water and brine, dried and then evaporated to yield a brown oil. This was purified by column chromatography on Merck 9385 silica eluting initially with dichloromethane through to a 50:1 mixture of dichloromethane:methanol to yield a brown foam. The brown foam was further purified by gradient elution HPLC (water-acetonitrile-trifluoroacetic acid) to give 5-[(2,6-difluoro-4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one as a yellow foam.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water and brine
  5. customdried
  6. customevaporated
  7. customto yield a brown oil
  8. customThis was purified by column chromatography on Merck 9385 silica eluting initially with dichloromethane through to a 50:1 mixture of dichloromethane
  9. custommethanol to yield a brown foam
  10. customThe brown foam was further purified by gradient elution HPLC (water-acetonitrile-trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-1a51447f1b804e9597a1ee27a4397a91
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05578630

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