Dimethylformamide → 2-Bromo-6-chlorobenzaldehyde

HRID 1241917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241917
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.CN(C)[CH:23]=[O:24]>O1CCCC1.O.C(O)(=O)C>[Cl:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([Br:13])[C:15]=1[CH:23]=[O:24]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 79281-Bromo-3-chlorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 135240422-Bromo-6-chlorobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 1.6 molar solution of butyllithium in hexanes was placed in a three-neck flask equipped with a stirrer, addition funnel, low-temperature thermometer and nitrogen inlet tube at 0° C. A solution of diisopropyl amine in anhydrous tetrahydrofuran was added dropwise. The resulting solution was stirred at 0° C. for ten minutes, then cooled to −78° C. Upon cooling, a solution of 1-bromo-3-chlorobenzene in anhydrous tetrahydrofuran was added dropwise. The reaction was stirred at −78° C. for one hour. Anhydrous dimethylformamide was added. The solution was allowed to slowly warm to room temperature, followed by the addition of acetic acid and water. The aqueous mixture was extracted with ether twice and the ether layers were separated. The combined ether layers were successively washed with aqueous hydrochloric acid and brine. The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel, eluting with hexanes-ethyl acetate to yield 2-chloro-6-bromobenzaldehyde.

Aufarbeitung

  1. customequipped with a stirrer, addition funnel
  2. customat 0° C
  3. temperaturecooled to −78° C
  4. temperatureUpon cooling
  5. stirringThe reaction was stirred at −78° C. for one hour
  6. temperatureto slowly warm to room temperature
  7. extractionThe aqueous mixture was extracted with ether twice
  8. customthe ether layers were separated
  9. washThe combined ether layers were successively washed with aqueous hydrochloric acid and brine
  10. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by flash column chromatography on silica gel
  14. washeluting with hexanes-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-92d46a1bf652487cab211f27338bece2
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115642B2

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