Hydrochloric Acid → 1-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

HRID 601608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601608
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[C:9]([N+]([O-])=O)[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].Cl.C1C[O:22]CC1>O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](=[O:22])[CH3:10])[CH:5]=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 665884842-Fluoro-1-methanesulfonyl-4-(2-nitro-propenyl)-benzene

Produkt 1

HCID 573512781-(3-Fluoro-4-(methylsulfonyl)phenyl)propan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Iron powder (25 g, 0.45 mol) is added to a stirred mixture of freshly prepared 2-fluoro-1-methanesulfonyl4-(2-nitro-propenyl)-benzene (Example AA2) (29 g, 0.112 mol) in THF (50 ml). Water (110 ml) is added and the mixture is heated to 60° C. Concentrated hydrochloric acid (50 ml) is added slowly over 1 h at 60-90° C. The reaction is then stirred at 100° C. for 20 hours then diluted with cold water (500 ml) and filtered through Celite™ filter material washing with chloroform (500 ml). he organic extract is washed with water (200 ml) followed by brine (200 ml). After drying (MgSO4) the mixture is absorbed on silica and purified by chromatography, eluting with hexane-ethyl acetate (1:1) to give the titled compound.

Aufarbeitung

  1. filtrationfiltered through Celite™
  2. filtrationfilter material
  3. washwashing with chloroform (500 ml)
  4. extractionhe organic extract
  5. washis washed with water (200 ml)
  6. dry with materialAfter drying (MgSO4) the mixture
  7. customis absorbed on silica
  8. custompurified by chromatography
  9. washeluting with hexane-ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-bf80821dc01e489d9ec732b1e1000875
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902375B2

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