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

HRID 2242618Notes

Reaction equation

HRID 2242618 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-380354cfb9584dc4aa70da9b71d08bb0
Source dataset
uspto-grants-2010_03
Patent number
US07671235B2

Reaction notes

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