Diphenyldimethoxysilane → Bisfluorenyldiphenylsilane

HRID 720223

Reaction equation

HRID 720223 reaction equation
BrC1C=CC2C3C(=CC(Br)=CC=3)[C:5]([CH2:24][CH2:25][CH2:26][CH2:27]CCCC)([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])C=2C=1.[CH2:32]([Li])[CH2:33][CH2:34][CH3:35].CO[Si:39](OC)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CCCCCC.C1(C)C=CC=CC=1.C(OCC)C>[C:35]1([Si:39]([C:20]2[C:19]3[CH2:18][C:17]4[C:26](=[CH:25][CH:24]=[CH:5][CH:16]=4)[C:27]=3[CH:23]=[CH:22][CH:21]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH2:35][C:25]3[C:32](=[CH:17][CH:16]=[CH:5][CH:24]=3)[C:33]=2[CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 81284DiphenyldimethoxysilaneHCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneHCID 178418339Butyllithium2×

Product 1

HCID 21889331Bisfluorenyldiphenylsilane

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Procedure

Under a nitrogen gas atmosphere, 4.90 g (8.94 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, 6.1 ml (9.76 mmol) of a hexane solution of n-butyllithium (1.6 M) was added dropwise. As the hexane solution of butyllithium was added dropwise, the solution turned red. The solution was agitated “as is” for approximately 1 hour; then, 1.03 g (4.21 mmol) of dimethoxydiphenylsilane was added, and this mixture was reacted under agitation 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. customthis mixture was reacted under agitation all night

Sources & evidence

ORD record
ord-e611839db2254d5c9b9ab4899234630d
Source dataset
uspto-grants-2006_11
Patent number
US07135242B2

Linked notes

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