Reaction #586151

Reaction equation

1-chloro-3-iodobenzene

3,5-dichloro-4-fluorobenzotrifluoride

water

→

1-chloro-3-(2,6-dichloro-4-trifluoromethylphenyl)benzene

Yield 36.7%

Solvents

benzene

n-butyllithium

hexane

Conditions

Workup

1. 1
   workup.STIRRINGAfter another 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 200 ml of water twice
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   OtherPurification of the residue by silica gel column chromatography

Procedure

To 10.0 g (41.9 mmol) of 1-chloro-3-iodobenzene in 50 ml of dry benzene, 32.0 ml of a n-butyllithium solution in hexane (1.56 mol/l) was added dropwise in a nitrogen stream at room temperature with stirring. After another 2 hours of stirring at room temperature, 9.9 g (42.5 mmol) of 3,5-dichloro-4-fluorobenzotrifluoride was added dropwise at 10° C. After another 12 hours of stirring at room temperature, the reaction mixture was poured into 500 ml of water for separation. The organic layer was washed with 200 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 5.0 g of 1-chloro-3-(2,6-dichloro-4-trifluoromethylphenyl)benzene (yield 35.0%).

Source