Silicon tetrachloride → 9,9-Dichloro-9-silafluorene

HRID 842492Notes

Reaction equation

HRID 842492 reaction equation
[Li].Br[C:3]1(Br)[CH2:8][CH:7]=[CH:6][CH:5]=[C:4]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Si:16](Cl)(Cl)([Cl:18])[Cl:17]>CCCCC.CCOCC>[Cl:17][Si:16]1([Cl:18])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:4]2[C:3]1=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 24816Silicon tetrachlorideHCID 3028194LithiumHCID 569236692,2 Dibromo-1,1-biphenyl

Product 1

HCID 6195839,9-Dichloro-9-silafluorene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8003PentaneSolvent

Procedure

Lithium wire (3.33 g, 0.08 mol) was washed with pentane, carefully cut into small pieces, and suspended in 150 mL of Et2O. While stirring, 2,2-dibromobiphenyl (25 g, 0.08 mol) 100 mL of diethyl ether was added dropwise over 1 hour and the contents were allowed to stir for 10 hours. The mixture was filtered through a frit to remove any unreacted Li and LiBr. The filtrated was loaded into an addition funnel and slowly dropped into a solution containing SiCl4 (50 g, 0.08 mol) in 200 mL of Et2O. After addition, the contents were stirred at room temperature for 5 hours. The solvent was removed in vacuo and 300 mL of pentane was added. The solution was filtered to remove LiCl and the solvents were again removed in vacuo. The solids were then loaded into a sublimator and allowed to sublime at 150° C. under full vacuum. Yield was 10.0 g (51%).

Workup

  1. stirringto stir for 10 hours
  2. filtrationThe mixture was filtered through a frit
  3. customto remove any unreacted Li and LiBr
  4. customThe filtrated was loaded into an addition funnel
  5. additionslowly dropped into a solution
  6. additionAfter addition
  7. stirringthe contents were stirred at room temperature for 5 hours
  8. customThe solvent was removed in vacuo and 300 mL of pentane
  9. additionwas added
  10. filtrationThe solution was filtered
  11. customto remove LiCl
  12. customthe solvents were again removed in vacuo
  13. customto sublime at 150° C. under full vacuum

Sources & evidence

ORD record
ord-14d641e7b3d64276a6490ba22ce0af47
Source dataset
uspto-grants-2002_04
Patent number
US06376412B1

Reaction notes

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