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

HRID 844459Notes

Reaction equation

HRID 844459 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 2 hours. 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-b460b035fe5241418909cf538fee38a8
Source dataset
uspto-grants-2002_04
Patent number
US06380334B1

Reaction notes

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