Sodium Iodide → 4-Iodophenylsulfur Pentafluoride

HRID 926107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926107
[Na+].[I-:2].F[B-](F)(F)F.[F:8][S:9]([F:21])([F:20])([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([N+]#N)=[CH:12][CH:11]=1.[C:22]1([O:28][CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[I:2][C:13]1[CH:14]=[CH:15][C:10]([S:9]([F:21])([F:20])([F:19])([F:18])[F:8])=[CH:11][CH:12]=1.[CH3:29][O:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:13]1[CH:14]=[CH:15][C:10]([S:9]([F:21])([F:20])([F:19])([F:18])[F:8])=[CH:11][CH:12]=1.[CH3:29][O:28][C:22]1[CH:23]=[C:24]([C:13]2[CH:14]=[CH:15][C:10]([S:9]([F:21])([F:20])([F:19])([F:18])[F:8])=[CH:11][CH:12]=2)[CH:25]=[CH:26][CH:27]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 7519AnisoleHCID 10340Sodium CarbonateHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Produkt 3

HCID 27791994-Iodophenylsulfur PentafluorideAusbeute 48 %HCID 1186563663-Methoxy-4'-(pentafluorosulfanyl)biphenylAusbeute 1 %HCID 1186563682-Methoxy-4'-(pentafluorosulfanyl)biphenylAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

NaI (22.0 mg, 0.147 mmol) was added portion-wise to a solution of 1 (31.0 mg, 0.0974 mmol) and anisole (96.0 mg, 0.888 mmol) in CH3CN (53.5 mg). The reaction mixture was neutralized with Na2CO3 and filtered through Celite 545 using hexane. The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane afforded 25b (15.3 mg, 48%), 2-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (4.0 mg, 13%), 3-methoxy-4′-(pentafluorosulfanyl) biphenyl as a colorless oil (0.2 mg, 1%), a fraction containing both 3-methoxy-4′-(pentafluorosulfanyl)biphenyl and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl (1:1) as colorless oil (2.0 mg, 7%), and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (0.7 mg, 2%).

Aufarbeitung

  1. filtrationfiltered through Celite 545
  2. customThe solvent was evaporated
  3. customto give a pale yellow oil, Silica column chromatography with hexane

Quellen und Nachweise

ORD-Eintrag
ord-51149eefaf1a48a684d9bbfb23ddddff
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284336B1

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