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

HRID 2364924Notes

Reaction equation

HRID 2364924 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-5fd8a701cedf4adb84658df9516d88b2
Source dataset
uspto-grants-2014_04
Patent number
US08697255B2

Reaction notes

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