9,9-Dichloro-9-silafluorene → 5H-benzo[b][1]benzosilole

HRID 843526Notes

Reaction equation

HRID 843526 reaction equation
CC1C([Li])C2C(C=1)=CC=CC=2.Cl[Si:13]1(Cl)[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2>CCOCC>[CH:15]1[C:14]2[SiH2:13][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6195839,9-Dichloro-9-silafluoreneHCID 178506826HCID 178506826, compound

Product 1

HCID 1009741605H-benzo[b][1]benzosilole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Solid 2-Methylindenyl lithium (3.34 g, 24.52 mmol) was added to a stirred solution of 9,9-Dichloro,9-silafluorene (3.08 g, 12.26 mmol) in Et2O (ca. 25 mL) and the resultant mixture was stirred at room temperature for 2hours. The solvent was removed and the residue was extracted into CH2Cl2 (ca. 75 mL), filtered and the solvent removed giving a white powder which was washed with pentane (ca 50 mL) and dried under vacuum leaving 9-Silafluorene, 9,9-bis-2-Methylindene as a white powder (3.80 g, 71%).

Workup

  1. customThe solvent was removed
  2. extractionthe residue was extracted into CH2Cl2 (ca. 75 mL)
  3. filtrationfiltered
  4. customthe solvent removed
  5. customgiving a white powder which
  6. washwas washed with pentane (ca 50 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2a61c24b5ade42e58940e19347b3237a
Source dataset
uspto-grants-2002_04
Patent number
US06380121B1

Reaction notes

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