Reaction #3999

Reaction equation

dry ice acetone

2,2-bis(4-bromophenyl)hexafluoropropane

n-butyllithium

chlorotrimethylsilane

→

2,2-bis(4-trimethylsilylphenyl)hexafluoropropane

Solvents

hexane

tetrahydrofuran

hexane

Conditions

Workup

1. 1
   Otherwas then made to the reaction mixture at -78° C
2. 2
   WashThe organic layer was washed with 2×150 ml saturated sodium chloride solution and 2×150 ml water
3. 3
   OtherThe organic layer was dried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated

Procedure

To a solution of 4.62 g (0.1 mole) 2,2-bis(4-bromophenyl)hexafluoropropane in 75 ml of anhydrous tetrahydrofuran was added dropwise 28 ml (0.4 moles) of a 1.4 molar solution of n-butyllithium in hexane while the reaction mixture was cooled in a dry ice-acetone slush. The reaction mixture was stirred for one half hour at -78° C. A dropwise addition of chlorotrimethylsilane (5 ml, 0.04 moles) was then made to the reaction mixture at -78° C. The stirring slurry was allowed to come to ambient temperature over 16 hours. To the reaction mixture was added 100 ml hexane. The organic layer was washed with 2×150 ml saturated sodium chloride solution and 2×150 ml water. The organic layer was dried, filtered, and concentrated to yield the white crystalline product 2,2-bis(4-trimethylsilylphenyl)hexafluoropropane.

Source