Sodium Iodide → 4-Iodophenylsulfur Pentafluoride

HRID 926107Notes

Reaction equation

HRID 926107 reaction equation
[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

Participants

8

Reactant 4

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

Product 3

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-51149eefaf1a48a684d9bbfb23ddddff
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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