Carbon tetrabromide → 2,7-Dibromo-9-(dibromomethylidene)-9H-fluorene

HRID 393125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393125
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[C:22](=O)[C:23]2[C:31](=[CH:32][CH:33]=1)[C:30]1[C:25](=[CH:26][C:27]([Br:34])=[CH:28][CH:29]=1)[CH:24]=2.[C:36](Br)(Br)([Br:38])[Br:37]>O1CCCC1>[Br:20][C:21]1[CH:33]=[CH:32][C:31]2[C:30]3[C:25](=[CH:26][C:27]([Br:34])=[CH:28][CH:29]=3)[C:24](=[C:36]([Br:38])[Br:37])[C:23]=2[CH:22]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53420103HCID 53420103, Verbindung

Produkt 1

HCID 226485382,7-Dibromo-9-(dibromomethylidene)-9H-fluoreneAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Triphenylphosphine (34.89 g, 133.0 mmol) was added to a solution of 2,7-dibromofluorenone (17.94 g, 53.08 mmol) in anhydrous tetrahydrofuran (550 mL) under nitrogen and the reaction mixture was heated at just below reflux with stirring. A solution of carbon tetrabromide (35.16 g, 106.0 mmol) in anhydrous tetrahydrofuran (150 mL) was added dropwise over 1.5 h, and the reaction mixture was heated at reflux for 17 h with stirring. After cooling to room temperature, the solvent was removed under reduced pressure and dichloromethane was added forming a slurry. The solid was filtered off and washed with dichloromethane. Recrystallisation of the solid from dichloromethane afforded 2,7-dibromo-9-dibromomethylene-fluorene (2) (15.30 g, 58%) as a bright orange powder, purity 100% (GC): υmax (KBr, cm−1) 3115, 3066, 1605, 1566, 1547, 1450, 1399, 1264, 1073; 1H and 13C NMR spectra as expected; M+=494 (pent).

Aufarbeitung

  1. temperaturethe reaction mixture was heated at just
  2. temperaturebelow reflux
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 17 h
  5. stirringwith stirring
  6. customthe solvent was removed under reduced pressure and dichloromethane
  7. additionwas added
  8. customforming a slurry
  9. filtrationThe solid was filtered off
  10. washwashed with dichloromethane
  11. customRecrystallisation of the solid from dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-9ed233fdd314430aad401a8a4f1e678a
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06805922B2

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