Chlorosuccinimide → 6'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-one

HRID 1619100

Reaktionsgleichung

Reaktionsgleichung von HRID 1619100
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][C:11]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 127170906'-Bromospiro[cyclopentane-1,3'-indolin]-2'-one

Produkt 1

HCID 669540836'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-oneAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N-Chlorosuccinimide (0.50 g, 3.75 mmol) was added to a solution of 6′-bromospiro[cyclopentane-1,3′-indolin]-2′-one (preparation 2, 0.20 g, 0.75 mmol) in chloroform (5 mL). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction and the mixture was extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (4:1 hexanes/ethyl acetate) gave the title compound (0.17 g, 75%) as a white solid.

Aufarbeitung

  1. temperatureheated to reflux
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification of the residue by flash chromatography (4:1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-45ada024ac554c368d201ecc32af279a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772288B2

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