9-Bromofluorene → 9-azido-9H-fluorene

HRID 541007

Reaction equation

HRID 541007 reaction equation
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]

Participants

5

Reactant 2

HCID 160249-BromofluoreneHCID 33557Sodium Azide

Product 1

HCID 43300859-azido-9H-fluoreneYield 87.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6661303eaa094c25ae818759c7672fe8
Source dataset
uspto-grants-2014_10
Patent number
US08871916B2

Linked notes

Loading…