Hexane → HCID 68386564, compound

HRID 1429118Notes

Reaction equation

HRID 1429118 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.CCCCCC.C([Li])CCC.[Cl:27][Si:28](Cl)([Cl:30])[Cl:29]>C(OCC)C>[Cl:27][Si:28]([Cl:30])([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

Participants

6

Reactant 4

HCID 8058HexaneHCID 24816Silicon tetrachlorideHCID 6201361-Bromo-3,5-di-tert-butylbenzeneHCID 178418339Butyllithium

Product 1

HCID 68386564HCID 68386564, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, to a diethyl ether solution (175 mL) of 1-bromo-3,5-di-tert-butylbenzene (35.00 g, 130.00 mmol), a 1.65 M hexane solution of n-butyllithium (88.67 mL, 143.00 mmol) was added dropwise at −78° C. After the mixture was gradually warmed to room temperature, stirring was performed at room temperature for 2 hours. The resultant mixture was added dropwise to a solution of tetrachlorosilane (66.26 g, 390.00 mmol) dissolved in diethyl ether (58 mL) at −78° C. After the mixture was gradually warmed to room temperature, stirring was performed at room temperature for 3 hours. 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. Purification by distillation under reduced pressure afforded trichloro(3,5-di-tert-butylphenyl)silane (24.11 g, yield 57.3%).

Workup

  1. temperatureAfter the mixture was gradually warmed to room temperature
  2. stirringstirring
  3. waitwas performed at room temperature for 3 hours
  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
  9. customPurification
  10. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-45a6703966694c29ad407753ee901e66
Source dataset
uspto-grants-2015_01
Patent number
US08937195B2

Reaction notes

Loading…