Dichlorodimethylsilane → 9-(Chlorodimethylsilyl)-9h-fluorene

HRID 411109Notes

Reaction equation

HRID 411109 reaction equation
Cl[Si:2]([Cl:5])([CH3:4])[CH3:3].[C:6]1([Li])[C:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1>CCCCCC>[Cl:5][Si:2]([CH3:3])([CH3:4])[CH:17]1[C:18]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[C:11]2[C:16]1=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 6398DichlorodimethylsilaneHCID 178506660HCID 178506660, compound

Product 1

HCID 5648779-(Chlorodimethylsilyl)-9h-fluoreneYield 90.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Into a 3000 ml flask, under nitrogen, was placed a solution of dichlorodimethyl silane (80.2 ml, 0.64 mol.) in 1000 ml of dry hexane, and the solution was Dre-cooled to −78° C. A suspension of fluorenyllithium (53.13 g, 0.32 mol.) in 2000 ml of hexane was slowly added via a cannula and the reaction mixture was stirred for an additional one hour at this temperature. The resulting mixture was gradually allowed to warm to room temperature and stirred for another 16 hours. The reaction mixture was then filtered under nitrogen, through a Celite plug (250 ml). The filtrate was concentrated and kept at −20° C. overnight. The resulting light-green crystals were recrystallised from hexane at −20° C. to afford 75.09 g (90.68 % yield) of chlorodimethyl-(9-fluorenyl)silane.

Workup

  1. customInto a 3000 ml flask, under nitrogen, was placed
  2. additionwas slowly added via a cannula
  3. stirringstirred for another 16 hours
  4. filtrationThe reaction mixture was then filtered under nitrogen, through a Celite plug (250 ml)
  5. concentrationThe filtrate was concentrated
  6. waitkept at −20° C. overnight
  7. customThe resulting light-green crystals were recrystallised from hexane at −20° C.

Sources & evidence

ORD record
ord-6e7b1a736c3d4db5aca6cfb5479697c8
Source dataset
uspto-grants-2003_05
Patent number
US06559089B1

Reaction notes

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