Fluorene → HCID 22623341, compound

HRID 840399Notes

Reaction equation

HRID 840399 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Li].[CH2:16]([Si:20]([CH2:23][CH2:24][CH2:25][CH3:26])(Cl)Cl)[CH2:17][CH2:18][CH3:19].[Cl-].[NH4+]>C(OCC)C>[CH2:16]([Si:20]([CH2:12][CH2:11][CH2:10][CH3:9])([CH:23]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:24]1=[CH:25][CH:26]=[CH:8][CH:7]=2)[CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 6853Fluorene2×HCID 25517Ammonium ChlorideHCID 76989Silane, dibutyldichloro-HCID 178418348HCID 178418348, compound

Product 1

HCID 22623341HCID 22623341, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

Fluorene (23.27 g, 140 mmol) was dissolved in 100 mL diethyl ether and the solution was cooled to −78° C. Methyllithium (1.4M in diethyl ether, 140 mL) was added dropwise to the stirred solution while maintaining the temperature at −78° C. After the addition was complete, the solution was allowed to warm to room temperature. Stirring was continued overnight. In a separate flask, di-n-butyldichlorosilane (14.9 g, 70 mmol) was dissolved in 50 mL diethyl ether. The temperature was reduced to −78° C., and the solution (prepared above) containing the fluorene anion was added to this stirred solution, dropwise. After the addition was complete, the reaction was allowed to warm slowly to room temperature and stirred overnight. The reaction was then treated with a saturated solution of ammonium chloride, the organic layer was collected and dried over magnesium sulfate, and dried in vacuo. The material was further purified by washing with methanol and drying in vacuo. Yield: 23.39 g (70.7%, 97% purity by GCMS). 1H-NMR (CD2Cl2), d, ppm: 7.81 (d, 4H), 7.30 (m, 12H), 3.95(s, 2H), 1.05(m, 4H), 0.85(m, 10H), 0.5(m, 4H).

Workup

  1. temperaturewhile maintaining the temperature at −78° C
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. customwas reduced to −78° C.
  5. customthe solution (prepared above)
  6. additionwas added to this stirred solution
  7. additionAfter the addition
  8. temperatureto warm slowly to room temperature
  9. stirringstirred overnight
  10. customthe organic layer was collected
  11. dry with materialdried over magnesium sulfate
  12. customdried in vacuo
  13. customThe material was further purified
  14. washby washing with methanol
  15. customdrying in vacuo

Sources & evidence

ORD record
ord-15ac3486be9b4f5cba9892077d99ddef
Source dataset
uspto-grants-2002_04
Patent number
US06365764B1

Reaction notes

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