Reaction #586128

Reaction equation

water

3-iodophenyl isopropyl sulfide

n-butyllithium

3,5-dichloro-4-fluorobenzotrifluoride

→

[3-(2,6-dichloro-4-trifluoromethylphenyl)phenyl] isopropyl sulfide

Yield 38.0%

Solvents

benzene

hexane

diethyl ether

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   OtherThe resulting reaction mixture
3. 3
   Temperaturecooled to 10° C.
4. 4
   OtherThe resulting reaction mixture
5. 5
   workup.STIRRINGwas stirred at room temperature for further 12 hours
6. 6
   WashThe organic layer was washed with 50 ml of water twice
7. 7
   Dryingdried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   OtherPurification of the residue by silica gel column chromatography

Procedure

1.0 g (3.6 mmol) of 3-iodophenyl isopropyl sulfide was stirred in 10 ml of dry benzene in a nitrogen stream at room temperature, while 2.8 ml of a n-butyllithium solution in hexane (1.56 mol/l) was added dropwise. The resulting reaction mixture was stirred at room temperature for another 2 hours and cooled to 10° C., and 1.0 g (4.3 mmol) of 3,5-dichloro-4-fluorobenzotrifluoride in 50 ml of diethyl ether was added dropwise. The resulting reaction mixture was stirred at room temperature for further 12 hours and 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, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.5 g of [3-(2,6-dichloro-4-trifluoromethylphenyl)phenyl] isopropyl sulfide (yield 38.0%) as a colorless liquid (nD20 1.5675).

Source