9-Bromofluorene → 9-azido-9H-fluorene

HRID 1803043

Reaktionsgleichung

Reaktionsgleichung von HRID 1803043
Br[CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N-:15]=[N+:16]=[N-:17].[Na+]>CC(C)=O.O>[N:15]([CH:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N+:16]=[N-:17]

Komponenten

5

Edukt 2

HCID 160249-BromofluoreneHCID 33557Sodium Azide

Produkt 1

HCID 43300859-azido-9H-fluoreneAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

9-Bromo-9H-fluorene (1.00 g, 4.08 mmol) was dissolved in acetone (7 mL). To this was added a solution of NaN3 (1.33 g, 20.4 mmol) in H2O (3 mL). The resulting solution was stirred overnight. Acetone was removed by concentration under reduced pressure. The resulting aqueous mixture was extracted with CH2Cl2 (2×15 mL), and the organic layers were combined, dried over Na2SO4(s), filtered, and concentrated under reduced pressure. The resulting solid residue was purified by silica gel flash chromatography, eluting with hexanes, to give azide 2j as a white solid (0.74 g, 3.57 mmol, 87% yield).

Aufarbeitung

  1. customAcetone was removed by concentration under reduced pressure
  2. extractionThe resulting aqueous mixture was extracted with CH2Cl2 (2×15 mL)
  3. dry with materialdried over Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid residue was purified by silica gel flash chromatography
  7. washeluting with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-736cbc4d046a440c933f1460102282c7
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08350014B2

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