Oxalyl chloride → 4-Chloro-3-fluoro-5-nitrobenzonitrile

HRID 1258741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258741
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[C:15]=1O)[C:11]#[N:12]>CN(C=O)C>[Cl:4][C:15]1[C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[F:7]

Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 679577893-Fluoro-4-hydroxy-5-nitrobenzonitrile

Produkt 1

HCID 679578694-Chloro-3-fluoro-5-nitrobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

Oxalyl chloride (5.44 g; 42.8 mmol) was added dropwise to a solution of 3-fluoro-4-hydroxy-5-nitrobenzonitrile (3.9 g; 21 mmol) in DMF (40 mL) at −25° C. The mixture was stirred at −25° C. for 15 min and thereafter at 80° C. for 2.5 h. The mixture was slowly poured into ice, the precipitate was filtered off and the filtrate was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was combined with the precipitate and filtered through a plug of silica gel to give the sub-title compound.

Aufarbeitung

  1. waitat 80° C. for 2.5 h
  2. additionThe mixture was slowly poured into ice
  3. filtrationthe precipitate was filtered off
  4. extractionthe filtrate was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfiltered through a plug of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b41695da678e4b95ab774655d8b84587
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466186B2

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