Toluene → Bisfluorenyldimethylsilane

HRID 720224

Reaktionsgleichung

Reaktionsgleichung von HRID 720224
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9]C=3)[C:5]([CH2:24]CCCCCCC)(CCCCCCCC)[C:4]=2[CH:3]=1.[CH3:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C([Li])CCC.CO[Si:45](OC)([CH3:47])[CH3:46].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(OCC)C>[C:13]1([Si:45]([C:34]2[C:33]3[CH2:56][C:50]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:32]=3[CH:37]=[CH:36][CH:35]=2)([CH3:47])[CH3:46])[C:12]2[CH2:11][C:6]3[C:5](=[CH:24][CH:9]=[CH:8][CH:7]=3)[C:4]=2[CH:3]=[CH:2][CH:14]=1

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 8058HexaneHCID 66187DimethoxydimethylsilaneHCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneHCID 178418339Butyllithium2×

Produkt 1

HCID 17824987Bisfluorenyldimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Under a nitrogen gas atmosphere, 5.00 g (9.11 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, the solution turned red. This solution was agitated “as is” for approximately 1 hour; then, 520 mg (4.33 mmol) of dimethoxydimethylsilane was added, and the resulting mixture was agitated and reacted all night.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9f72a0a7edc6452e8c60dd11c8523788
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135242B2

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