1,1',1''-(Chlorosilylidyne)tris(benzene) → HCID 59720465, compound

HRID 387611Notes

Reaction equation

HRID 387611 reaction equation
CO[C:3]1[CH:4]=[C:5]([N:9]2[C:21]3[CH:20]=[CH:19][C:18]([Br:22])=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.Cl[Si:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl-].[NH4+]>C1COCC1>[Br:22][C:18]1[CH:19]=[CH:20][C:21]2[N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:5]3[C:6]([C:16]=2[CH:17]=1)=[CH:7][C:8]([Si:30]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[CH:3][CH:4]=3

Participants

6

Reactant 4

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 25517Ammonium ChlorideHCID 66661151HCID 66661151, compoundHCID 178418339Butyllithium2×

Product 1

HCID 59720465HCID 59720465, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 9-(3-methoxyphenyl)-3,6-dibromo-9H-carbazole (26 g, 1 eq) in dry THF (700 ml) is admixed slowly at −78° C. under argon with n-butyllithium (1.6 M in hexane, 41 ml, 1 eq) and stirred at −78° C. for 2 h. After a solution of chlorotriphenylsilane (30 g, 1.5 eq) in dry THF (150 ml) had been added at −78° C., the mixture was warmed to room temperature overnight with stirring. Excess butyllithium is hydrolyzed with saturated ammonium chloride solution. The precipitated reaction product is filtered off and washed thoroughly with methylene chloride. The combined methylene chloride filtrates are extracted with water and concentrated to dryness. The residue is stirred with acetone and filtered off. Yield 74%.

Workup

  1. temperaturethe mixture was warmed to room temperature overnight
  2. stirringwith stirring
  3. customThe precipitated reaction product
  4. filtrationis filtered off
  5. washwashed thoroughly with methylene chloride
  6. extractionThe combined methylene chloride filtrates are extracted with water
  7. concentrationconcentrated to dryness
  8. stirringThe residue is stirred with acetone
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-e8169a3374a24c7486609b90530d0561
Source dataset
uspto-grants-2013_02
Patent number
US08373159B2

Reaction notes

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