Toluene → 1,2-Bisfluorenyltetramethyldisilane

HRID 720225

Reaction equation

HRID 720225 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5](CCCCCCCC)(CCCCCCCC)[C:4]=2[CH:3]=1.[CH3:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C([Li])CCC.Cl[Si:44]([CH3:50])([CH3:49])[Si:45]([CH3:48])([CH3:47])Cl.[C:51]1([CH3:57])[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C(OCC)C>[C:13]1([Si:44]([CH3:50])([CH3:49])[Si:45]([CH3:48])([CH3:47])[C:34]2[C:33]3[CH2:57][C:51]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:32]=3[CH:37]=[CH:36][CH:35]=2)[C:12]2[CH2:11][C:6]3[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:4]=2[CH:3]=[CH:2][CH:14]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8058HexaneHCID 780451,2-Dichloro-1,1,2,2-tetramethyldisilaneHCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneHCID 178418339Butyllithium2×

Product 1

HCID 218893331,2-Bisfluorenyltetramethyldisilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen gas atmosphere, 4.99 g (9.10 mmol) of 2,7-dibromo-9,9-dioctylfluorene, 20 ml of diethyl ether and 10 ml of toluene were added to a 100 ml three-necked flask equipped with a reflux condenser and a dropping funnel. Under cooling by an ice bath, 6.2 ml (9.92 mmol) of a hexane solution of n-butyllithium (1.6 M) was added dropwise. As the butyllithium was added dropwise, the solution turned red. This solution was agitated “as is” for approximately 1 hour; then, 810 mg (4.33 mmol) of 1,2-dichlorotetramethyldisilane was added, and the resulting mixture was agitated and reacted all night.

Workup

  1. customequipped with a reflux condenser and a dropping funnel
  2. temperatureUnder cooling by an ice bath
  3. customfor approximately 1 hour
  4. stirringthe resulting mixture was agitated
  5. customreacted all night

Sources & evidence

ORD record
ord-213509883d0a4b648c0eeb2ca8191239
Source dataset
uspto-grants-2006_11
Patent number
US07135242B2

Linked notes

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