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Tetrabutylammonium Fluoride → N-(4-Bromo-2-iodophenyl)benzenesulfonamide

HRID 400588
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 400588
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([S:25]([N:28](S(C2C=CC=CC=2)(=O)=O)[C:29]2[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=2[I:36])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.C(OCC)(=O)C.Cl>[Br:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[C:30]([I:36])[CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 60026850N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)

Produkt 1

HCID 60026307N-(4-Bromo-2-iodophenyl)benzenesulfonamideAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

A solution of tetrabutylammonium fluoride (1 M in THF, 11 mL) in 30 mL of THF was treated with N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline) (5.78 g, 10 mmol) in several portions. After 18 hours, the mixture was diluted with of 40 mL of ethyl acetate and 40 mL of 1 N HCl. The phases were separated and the aqueous layer was extracted with two 40 mL portions of ethyl acetate. The combined organic layers were washed with two 20 mL portions of 1 N HCl, two 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3.95 g (90% yield) of the title compound as a solid, which was used without further purification.

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with two 40 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with two 20 mL portions of 1 N HCl, two 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f48f7c3ff64b4f578e03f54458b9a514
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08741897B2

Notizen zur Reaktion

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