1,1',1''-(Chlorosilylidyne)tris(benzene) → HCID 58131120, compound

HRID 387614Notes

Reaction equation

HRID 387614 reaction equation
[Li][C:2]([CH3:5])([CH3:4])C.Br[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([Si:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][C:15](Br)=[CH:14][CH:13]=3.Cl[Si:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[NH4+].[Cl-]>C1COCC1>[C:28]1([Si:21]([C:4]2[CH:2]=[CH:5][CH:8]=[CH:7][CH:19]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:7]2[CH:8]=[CH:9][C:10]3[N:11]([Si:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([Si:41]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:14][CH:13]=4)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 25517Ammonium ChlorideHCID 58131163HCID 58131163, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 58131120HCID 58131120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

tert-BuLi (1.7 M in pentane, 58 ml, 99 mmol) is added slowly to a cold solution (−78° C.) of 3,6-dibromo-9-triphenylsilylcarbazole (90% purity, see i), 13 g, 22 mmol) in dry THF (1000 ml). After stirring at −78° C. for two hours, ClSiPh3 (34 g, 115 mmol) in dry THF is added. 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. After column chromatography (SiO2; 5:1 cyclohexane:CH2Cl2), the pure product is obtained (Rf˜0.3, 11 g, 53%).

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. customAfter column chromatography (SiO2; 5:1 cyclohexane:CH2Cl2), the pure product is obtained (Rf˜0.3, 11 g, 53%)

Sources & evidence

ORD record
ord-b2e18cafc44449258b47267a1e40a487
Source dataset
uspto-grants-2013_02
Patent number
US08373159B2

Reaction notes

Loading…