Phenyltrichlorosilane → HCID 68386487, compound

HRID 1429120Notes

Reaction equation

HRID 1429120 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1.C([Li])CCC.[Cl:21][Si:22](Cl)([Cl:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)C.CCCCCC>[Cl:21][Si:22]([Cl:29])([C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7372PhenyltrichlorosilaneHCID 6201361-Bromo-3,5-di-tert-butylbenzeneHCID 178418339Butyllithium

Product 1

HCID 68386487HCID 68386487, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, to a diethyl ether solution (106 mL) of 1-bromo-3,5-di-tert-butylbenzene (10.60 g, 39.37 mmol), a 1.65 M hexane solution of n-butyllithium (23.86 mL, 39.37 mmol) was added dropwise at −78° C. After the mixture was gradually warmed to room temperature, stirring was performed at room temperature for 3 hours. The resultant mixture was added dropwise to a diethyl ether solution (106 mL) of trichlorophenylsilane (24.99 g, 118.12 mmol) at −78° C. After the mixture was gradually warmed to room temperature, stirring was performed at room temperature. After completion of the reaction, the solvent was removed under reduced pressure. Thereafter, hexane wad added to the residue, and insoluble materials were removed by filtration. The solvent was removed from the filtrate under reduced pressure. Trichlorophenylsilane was removed by heating to 100° C. under reduced pressure to obtain dichloro(3,5-di-tert-butylphenyl)(phenyl)silane (11.77 g, yield 81.8%).

Workup

  1. temperatureAfter the mixture was gradually warmed to room temperature
  2. stirringstirring
  3. customwas performed at room temperature
  4. customAfter completion of the reaction
  5. customthe solvent was removed under reduced pressure
  6. additionThereafter, hexane wad added to the residue, and insoluble materials
  7. customwere removed by filtration
  8. customThe solvent was removed from the filtrate under reduced pressure
  9. customTrichlorophenylsilane was removed
  10. temperatureby heating to 100° C. under reduced pressure

Sources & evidence

ORD record
ord-1e359be4d1be48afabc0e3f7d60f76f9
Source dataset
uspto-grants-2015_01
Patent number
US08937195B2

Reaction notes

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