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Benzoyl Peroxide → (Z)-2-(2-bromo-6-fluoro-1-indanylidene)acetamide

HRID 362860
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 362860
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[F:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][CH2:33]/[C:34]/2=[CH:37]\[C:38]([NH2:40])=[O:39])=[CH:30][CH:29]=1>C(Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[Br:1][CH:33]1[CH2:32][C:31]2[C:35](=[CH:36][C:28]([F:27])=[CH:29][CH:30]=2)/[C:34]/1=[CH:37]/[C:38]([NH2:40])=[O:39]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 9837001(E)-2-(6-fluoro-1-indanylidene)acetamide

Produkt 1

HCID 69887285(Z)-2-(2-bromo-6-fluoro-1-indanylidene)acetamideAusbeute 3,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel
HCID 5943
Carbon Tetrachloride
Lösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (22.57 g, 126.8 mmoles, Aldrich) and benzoyl peroxide (1.89 g, 7.8 mmoles, Aldrich) were added to a suspension of (E)-2-(6-fluoro-1-indanylidene)acetamide (21.00 g, 109.8 mmoles) in carbon tetrachloride (400 mL) and benzene (400 mL). The mixture was refluxed under a calcium chloride drying tube while shining an infrared lamp on it for two hours, after which time an orange solution formed. The heat and light were removed, and the solution was stirred at ambient temperature for 18 hours. The mixture was filtered, and the solids were washed with ethyl acetate. The washings and filtrate were combined and evaporated in vacuo. The residue was dissolved in ethyl acetate (800 mL) and washed with water (3×200 mL) and brine (200 mL), dried over sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed on silica gel eluting first with hexane: ethyl acetate (2:1) gradually increasing the polarity to hexane: ethyl acetate (1:1). The fractions containing the major spot were combined and evaporated in vacuo to give a yellow solid which was dried in a vacuum at 70° C. for 18 hours to give 1.022 g (3%) of (Z)-2-(2-bromo-6-fluoro-1-indanylidene)acetamide as a yellow solid, mp 162°-163° C. 1H-NMR

Aufarbeitung

  1. temperatureThe mixture was refluxed under a calcium chloride drying tube
  2. customfor two hours
  3. customafter which time an orange solution formed
  4. temperatureThe heat
  5. customlight were removed
  6. filtrationThe mixture was filtered
  7. washthe solids were washed with ethyl acetate
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in ethyl acetate (800 mL)
  10. washwashed with water (3×200 mL) and brine (200 mL)
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customThe residue was chromatographed on silica gel eluting first with hexane: ethyl acetate (2:1)
  15. temperaturegradually increasing the polarity to hexane: ethyl acetate (1:1)
  16. additionThe fractions containing the major spot
  17. customevaporated in vacuo
  18. customto give a yellow solid which
  19. customwas dried in a vacuum at 70° C. for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-ff68691440984ff491e21e96cc531dc9
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05872118

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