p-Terphenyl → 9-(Trichlorosilyl)methyl-2-phenylfluorene

HRID 1457372

Reaction equation

HRID 1457372 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al].Cl[CH:21](Cl)[CH2:22][Si:23]([Cl:26])([Cl:25])[Cl:24]>C(=S)=S.CCCCCC>[Cl:24][Si:23]([CH2:22][CH:21]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:11]=[CH:12][C:7]=2[C:1]2[C:2]1=[CH:3][CH:4]=[CH:5][CH:6]=2)([Cl:26])[Cl:25]

Participants

6

Reactant 3

HCID 7115p-TerphenylHCID 5359268AluminumHCID 19360808(2,2-Dichloroethyl)trichlorosilane

Product 1

HCID 221046079-(Trichlorosilyl)methyl-2-phenylfluoreneYield 10%

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolventHCID 8058HexaneSolvent2×

Procedure

In the same apparatus and procedures as Example 1 above, 5.0 g (21.7 mmol) of para-terphenyl and 0.30 g (11.1 mmol) of aluminum were alkylated in CS2 (50 ml) solution with (2,2-dichloroethyl)trichlorosilane 6.68 g (21.7 mmol) under dry nitrogen atmospheric pressure for 24 hrs at reflux temperature. Freshly distilled hexane (100 ml) was added to the reaction mixture and insoluble solids in hexane were filtered from the organic solution. After hexane and CS2 were distilled, recrystallization from ether yielded 0.85 g of 9-(trichlorosilyl)methyl-2-phenylfluorene (yield; 10%).

Workup

  1. customfor 24 hrs
  2. temperatureat reflux temperature
  3. filtrationwere filtered from the organic solution
  4. distillationAfter hexane and CS2 were distilled
  5. customrecrystallization from ether

Sources & evidence

ORD record
ord-44b5a1b2074441da9cd95f33c059751f
Source dataset
uspto-grants-1998_12
Patent number
US05847182

Linked notes

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