Perfluorobutanesulfonic acid → Diphenyliodanium nonafluorobutane-1-sulfonate

HRID 970264

Reaktionsgleichung

Reaktionsgleichung von HRID 970264
[Br-].[C:2]1([I+:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]([F:31])([F:30])[C:17]([F:29])([F:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[S:20]([OH:23])(=[O:22])=[O:21]>[Ag]=O.CO>[F:31][C:16]([F:15])([F:30])[C:17]([F:28])([F:29])[C:18]([F:26])([F:27])[C:19]([F:24])([F:25])[S:20]([O-:23])(=[O:22])=[O:21].[C:9]1([I+:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 67815Perfluorobutanesulfonic acidHCID 73871Iodonium, diphenyl-, bromide (1:1)

Produkt 1

HCID 16216934Diphenyliodanium nonafluorobutane-1-sulfonateAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To 100 ml of methanol, 3.61 g (0.01 mole) of diphenyliodonium bromide and 1.62 g (0.007 mole) of silver oxide were suspended, then the mixture was reacted at room temperature for 2 hours. To the reaction solution, 4.2 g (0.014 mole) of nonafluorobutanesulfonic acid was added drop-wise at room temperature, followed by reacting at the same temperature for 2 hours while stirring. The thus obtained reaction mixture was filtered and concentrated under reduced pressure, followed by purifying 6.4 g of the residue by column chromatography [Wako gel, C-200; eluent of methylene chloride/methanol=9/1 (v/v)], to obtain 4.6 g of diphenyliodonium nonafluorobutanesulfonate as a colorless crystal. The thus obtained crystal was named acid generator B1. The measurement results of melting point and NMR of acid generator B1 are shown bellow.

Aufarbeitung

  1. customthe mixture was reacted at room temperature for 2 hours
  2. customThe thus obtained reaction mixture
  3. filtrationwas filtered
  4. concentrationconcentrated under reduced pressure
  5. customby purifying 6.4 g of the residue by column chromatography [Wako gel, C-200; eluent of methylene chloride/methanol=9/1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-6c2008237a64455bb97166bc766e048d
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312014B2

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