Hydrochloric Acid → 5-Bromo-4-chloro-2-fluorotoluene

HRID 369240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369240
N(OCCCC)=O.[Br:8][C:9]1[CH:15]=[C:14]([CH3:16])[C:13]([F:17])=[CH:12][C:10]=1N.[ClH:18]>C(#N)C>[Br:8][C:9]1[C:10]([Cl:18])=[CH:12][C:13]([F:17])=[C:14]([CH3:16])[CH:15]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 27733792-Bromo-5-fluoro-4-methylaniline

Produkt 1

HCID 27732735-Bromo-4-chloro-2-fluorotoluene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Cupric chloride (6 g) and butyl nitrite (4.8 g) were added to acetonitrile (16 ml), and the mixture was stirred at 60° C. for 10 minutes. A solution of 2-bromo-5-fluoro-4-methylaniline (7.6 g) in acetonitrile (30 ml) was added dropwise to the mixture at the same temperature, and the resultant mixture was then stirred at the same temperature for 30 minutes. After the reaction mixture was allowed to cool, 2N hydrochloric acid was added to acidify the reaction mixture, and it was extracted with diethyl ether. After an organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was subjected to column chromatography on silica gel to conduct elution with n-hexane, thereby obtaining the title compound (5.6 g) as a pale yellow oil.

Aufarbeitung

  1. temperatureto cool
  2. extractionwas extracted with diethyl ether
  3. dry with materialAfter an organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washelution with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d21dca6fcecf40589c50774b204a76af
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136823

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