Sodium Iodide → 4-Iodophenylsulfur Pentafluoride

HRID 591378ノート

反応式

HRID 591378 の反応式
[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

参加物

8

反応物 4

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

生成物 3

HCID 27791994-Iodophenylsulfur Pentafluoride収率 48%HCID 1186563663-Methoxy-4'-(pentafluorosulfanyl)biphenyl収率 1%HCID 1186563682-Methoxy-4'-(pentafluorosulfanyl)biphenyl収率 13%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-00ffd0431bd948c19cf401d09bb32075
出典データセット
uspto-grants-2016_01
特許番号
US09238660B1

反応ノート

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