Réaction #586128

Équation de réaction

water

3-iodophenyl isopropyl sulfide

n-butyllithium

3,5-dichloro-4-fluorobenzotrifluoride

→

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

Rendement 38.0%

Solvants

benzene

hexane

diethyl ether

Conditions de réaction

Traitement

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

Mode opératoire

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