Iodine → HCID 66733550, Verbindung

HRID 403011

Reaktionsgleichung

Reaktionsgleichung von HRID 403011
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:25]I>C(Cl)(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:14]([I:25])=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][OH:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 807IodineHCID 743383,4-Bis(benzyloxy)benzyl alcohol

Produkt 1

HCID 66733550HCID 66733550, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76299Silver trifluoroacetateKatalysatorHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

The dibenzyloxybenzyl alcohol 28 (21.44 mmol) and silver trifluoroacetate (21.44 mmol) were suspended in 100 mL of dry chloroform and stirred under argon. A solution of iodine (21.44 mmol) in dry chloroform (50 mL) was added to the suspension dropwise at room temperature. The reaction mixture was then stirred for a further period of 2 h and filtered. The filtrate was washed with 20% sodium thiosulfate solution in water. The organic layer was separated and dried over anhydrous Na2SO4. Filtration was followed by evaporation of the chloroform solution resulting in the pure iodo compound, 3,4-Dibenzyloxy-6-iodobenzyl alcohol (29), as a pale yellow solid in 84% yield.

Aufarbeitung

  1. stirringThe reaction mixture was then stirred for a further period of 2 h
  2. filtrationfiltered
  3. washThe filtrate was washed with 20% sodium thiosulfate solution in water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationFiltration
  7. customwas followed by evaporation of the chloroform solution

Quellen und Nachweise

ORD-Eintrag
ord-ecb27ec953764accb3730e698a8568d6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742139B2

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