4-Bromobiphenyl → 2-Bromo-9-(trichlorosilyl)methylfluorene

HRID 1457374Notes

Reaction equation

HRID 1457374 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Al].Cl[CH:16](Cl)[CH2:17][Si:18]([Cl:21])([Cl:20])[Cl:19]>C(=S)=S.CCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:16]([CH2:17][Si:18]([Cl:21])([Cl:20])[Cl:19])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 71014-BromobiphenylHCID 5359268AluminumHCID 19360808(2,2-Dichloroethyl)trichlorosilane

Product 1

HCID 221046082-Bromo-9-(trichlorosilyl)methylfluoreneYield 15%

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 4-bromobiphenyl and 0.08 g (11.1 mmol) of aluminum foil were alkylated in CS2 (50 ml) solution with (2,2-dichloroethyl)-trichlorosilane 6.68 g (21.7 mmol) for 24 hr. 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, the reaction products were vacuum distilled to give 1.28 g of 2-bromo-9-(trichlorosilyl)methylfluorene (yield; 15%).

Workup

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

Sources & evidence

ORD record
ord-0d8ec0c8224946758190bb6acad92d0b
Source dataset
uspto-grants-1998_12
Patent number
US05847182

Reaction notes

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