Reaktion #2743

ord-46318b77785946d0ac36cbc991b8c83d

Reaktionsgleichung

CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(OS(=O)(=O)C(F)(F)F)c(F)c2)CC1
(2,6-difluoro-4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate
[Cl-].[Li+]
lithium chloride
CN(C)C=O
N,N-dimethylformamide
CCCCCCC[Si]1(c2ccccc2)CCC(c2cc(F)c(CC(C)CC)c(F)c2)CC1
4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)-1-(2-methylbutyl)-2,6-difluorobenzene
Ausbeute 140.1%

Lösungsmittel

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto obtain an organizing reagent
  2. 2
    workup.ADDITIONThe reaction mixture was after-treated by a usual manner
  3. 3
    Sonstigepurified through chromatography

Vorschrift

3.0 g (20 mmols) of (S)-1-bromo-2-methylbutane was dropped in a mixture of 0.5 g (21 mmols) of magnesium and 50 ml of THF to obtain a Grignard reagent. This reagent was dropped in 20 ml of a THF solution of 2.8 g (20 mmols) of zinc chloride to obtain an organizing reagent. Subsequently, the solution was dropped in a mixture of 10.7 g (20 mmols) of (2,6-difluoro-4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, 100 mg of tetrakis(triphenylphosphine)palladium (0), 500 mg of lithium chloride and 50 ml of N,N-dimethylformamide, and agitated at 50° C. for 8 hours. The reaction mixture was after-treated by a usual manner and purified through chromatography to obtain 6.4 g (yield: 70%) of 4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)-1-(2-methylbutyl)-2,6-difluorobenzene.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05730902uspto-grants-1998_03