benzenethiol, potassium salt → 8-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

HRID 971296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 971296
F[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2.[C:14]1([S-:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[K+]>CS(C)=O.Cl>[F:12][C:10]1[CH:11]=[C:2]([S:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=[C:4]2[C:9]=1[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2

Komponenten

5

Edukt 2

HCID 11789364benzenethiol, potassium saltHCID 552745816,8-Difluoro-3,4-dihydronaphthalen-1(2H)-one

Produkt 1

HCID 590217698-fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 6,8-difluoro-3,4-dihydro-2H-naphthalen-1-one (1.0 gram, 5.5 moles) and potassium thiophenolate (0.81 gram, 5.5 mmole) in 4 mL DMSO was heated at 50° C. for 0.5 hour. The mixture was diluted with 30 mL 0.1N hydrochloric acid and then it was extracted with 50 mL diethyl ether. The organic phase was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. 8-Fluoro-6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one was obtained by recrystallization of the residue from ethyl acetate/hexane, 0.871 gram (58%), m.p. 112-113° C., M+H=273.

Aufarbeitung

  1. extractionit was extracted with 50 mL diethyl ether
  2. washThe organic phase was washed with water
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f627217d948420f9759db34425b15ca
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312359B2

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