1,1',1''-(Chlorosilylidyne)tris(benzene) → HCID 58131163, compound

HRID 2364926Notes

Reaction equation

HRID 2364926 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.Cl[Si:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH4+].[Cl-]>C1COCC1>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([Si:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Participants

6

Reactant 4

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 58131163HCID 58131163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (60% dispersion in oil, 1.5 g, 37 mmol) is added slowly to a cold solution (0° C.) of 3,6-dibromocarbazole (10.4 g, 31 mmol) in dry THF (1000 ml). After stirring for two hours, a solution of ClSiPh3 (18.7 g, 62 mmol) in dry THF (200 ml) is added at 0° C. The mixture is stirred overnight, and saturated NH4Cl solution is added. The resulting salt is filtered off, and the organic phase is separated from the aqueous phase. The aqueous phase is extracted with CH2Cl2. The organic phase is washed twice with water. The combined organic phases are dried over Na2SO4. Filtration through SiO2 gives the desired product (quantitative).

Workup

  1. stirringThe mixture is stirred overnight
  2. filtrationThe resulting salt is filtered off
  3. customthe organic phase is separated from the aqueous phase
  4. extractionThe aqueous phase is extracted with CH2Cl2
  5. washThe organic phase is washed twice with water
  6. dry with materialThe combined organic phases are dried over Na2SO4
  7. filtrationFiltration through SiO2

Sources & evidence

ORD record
ord-1e065c14a75a420eac7d72849ee23323
Source dataset
uspto-grants-2014_04
Patent number
US08697255B2

Reaction notes

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