Fluorobenzene → (4-Fluorophenyl)(pyridin-3-yl)methanone

HRID 258892

Reaktionsgleichung

Reaktionsgleichung von HRID 258892
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([C:15]2[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=2)=[O:9])[CH:4]=1

Komponenten

4

Edukt 3

HCID 10008FluorobenzeneHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 762660(4-Fluorophenyl)(pyridin-3-yl)methanone

Versuchsvorschrift

To a stirred and cooled (ice-bath) mixture of 88 parts of nicotinoyl chloride hydrochloride in 400 parts of fluorobenzene are added portionwise 165 parts of aluminium chloride at a temperature between 5° and 10° C. Upon completion, the cooling-bath is removed and the mixture is stirred and refluxed for 6 hours. The reaction mixture is allowed to stand overnight at room temperature and is then poured onto a mixture of crushed ice and hydrochloric acid. After cooling, the layers are separated. The aqueous phase is extracted three times with ether. The combined organic layers are discarded and the aqueous phase is alkalized with a 40% sodium hydroxide solution. The product is extracted several times with chloroform. The extracts are washed twice with water, dried and evaporated. The residue is dissolved in ether. The solution is filtered from insoluble matter and the filtrate is allowed to crystallize upon dilution with petroleumether at -20° C, yielding p-fluorophenyl 3-pyridyl ketone; mp. 74.5° C.

Aufarbeitung

  1. temperaturecooled
  2. customUpon completion, the cooling-bath is removed
  3. stirringthe mixture is stirred
  4. temperaturerefluxed for 6 hours
  5. additionis then poured onto a mixture of crushed ice and hydrochloric acid
  6. temperatureAfter cooling
  7. customthe layers are separated
  8. extractionThe aqueous phase is extracted three times with ether
  9. extractionThe product is extracted several times with chloroform
  10. washThe extracts are washed twice with water
  11. customdried
  12. customevaporated
  13. dissolutionThe residue is dissolved in ether
  14. filtrationThe solution is filtered from insoluble matter
  15. customto crystallize upon dilution with petroleumether at -20° C

Quellen und Nachweise

ORD-Eintrag
ord-7cd10ee66c434d639e0fda3f41bd9bf5
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04035376

Verknüpfte Notizen

Wird geladen…