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

HRID 339193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339193
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-b85f6381ee8a4ba98a01120c2a0c922d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889906B2

Notizen zur Reaktion

Wird geladen…