Reaction #586144

Reaction equation

4-iodotoluene

3,5-dichloro-4-fluorobenzotrifluoride

water

→

4-(2,6-dichloro-4-trifluoromethylphenyl)toluene

Yield 85.1%

Solvents

benzene

n-butyllithium

hexane

diethyl ether

Conditions

Workup

1. 1
   workup.STIRRINGAfter 2 hours of stirring at room temperature
2. 2
   workup.STIRRINGAfter another 12 hours of stirring at room temperature
3. 3
   WashThe organic layer was washed with 50 ml of water twice
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedure

To 5.7 g (26.1 mmol) of 4-iodotoluene in 30 ml of dry benzene, 17.0 ml of a n-butyllithium solution in hexane (1.60 mol/l) was added dropwise in a nitrogen stream at room temperature with stirring. After 2 hours of stirring at room temperature, 10 ml of 6.0 g (25.8 mmol) of 3,5-dichloro-4-fluorobenzotrifluoride in 10 ml of diethyl ether was added dropwise at 10° C. After another 12 hours of stirring at room temperature, the reaction mixture was poured into 100 ml of water for separation. The organic layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.7 g of 4-(2,6-dichloro-4-trifluoromethylphenyl)toluene (yield 85.0%) as a colorless liquid.

Source