HCID 68386487, compound → HCID 86708703, compound

HRID 1429121Notes

Reaction equation

HRID 1429121 reaction equation
[Cl:1][Si:2](Cl)([C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:24][C:25]1[CH:26]=[C:27]([Li])[CH:28]=[C:29]([CH3:31])[CH:30]=1>C(OCC)C>[Cl:1][Si:2]([C:9]1[CH:14]=[C:13]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:12]=[C:11]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=1)([C:27]1[CH:26]=[C:25]([CH3:24])[CH:30]=[C:29]([CH3:31])[CH:28]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 68386487HCID 68386487, compoundHCID 178506702HCID 178506702, compound2×

Product 1

HCID 86708703HCID 86708703, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, to a diethyl ether solution (70 mL) of dichloro(3,5-di-tert-butylphenyl)(phenyl)silane (7.00 g, 19.16 mmol), a solution of 3,5-dimethylphenyllithium (2.15 g, 19.16 mmol) dissolved in diethyl ether (22 mL) was added dropwise at −20° C. After the mixture was gradually warmed to room temperature, stirring was performed at room temperature. 3,5-Dimethylphenyllithium (1.26 g, 11.24 mmol) was added and further stirred at room temperature. After completion of the reaction, the solvent was removed under reduced pressure. Thereafter, hexane was added to the residue, and insoluble materials were removed by filtration. The solvent was removed from the filtrate under reduced pressure to obtain chloro(3,5-di-tert-butylphenyl)(3,5-dimethylphenyl)(phenyl)silane (7.21 g, yield 86.5%) as yellow oil.

Workup

  1. additionwas added dropwise at −20° C
  2. customwas performed at room temperature
  3. stirringfurther stirred at room temperature
  4. customAfter completion of the reaction
  5. customthe solvent was removed under reduced pressure
  6. additionThereafter, hexane was added to the residue, and insoluble materials
  7. customwere removed by filtration
  8. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-3b1bdff23e724aa693f63f9f87825d67
Source dataset
uspto-grants-2015_01
Patent number
US08937195B2

Reaction notes

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