Reaction #2743

Reaction equation

(2,6-difluoro-4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate

lithium chloride

N,N-dimethylformamide

→

4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)-1-(2-methylbutyl)-2,6-difluorobenzene

Yield 140.1%

Solvents

THF

Conditions

Workup

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

Procedure

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.

Source