反応 #53561

反応方程式

water

3-iodophenyl isopropyl sulfide

n-butyllithium

3,5-dichloro-4-fluorobenzotrifluoride

→

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

収率 38.0%

溶媒

benzene

hexane

diethyl ether

反応条件

後処理

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

実験手順

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).

出典