Reacción #53558

Ecuación de reacción

1,1′-thiodi-[2-ethoxymethoxy-5-(4-trifluoromethylphenyl)benzene]

Rongalite

potassium carbonate

2,2,2-trifluoroethyl iodide

→

(2-ethoxymethoxy-5-(4-trifluoromethylphenyl)phenyl] 2,2,2-trifluoroethyl sulfide

Rendimiento 151.1%

Disolventes

water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Extracciónextracted with 50 ml of ethyl acetate twice
3. 3
   LavadoThe ethyl acetate layer was washed with 50 ml of water twice
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
6. 6
   OtroPurification of the residue by silica gel column chromatography

Procedimiento

3.3 g (5.0 mmol) of 1,1′-thiodi-[2-ethoxymethoxy-5-(4-trifluoromethylphenyl)benzene], 3.0 g (19.5 mmol) of Rongalite, 3.0 g (21.7 mmol) of potassium carbonate and 3.2 g (17.6 mmol) of 2,2,2-trifluoroethyl iodide were stirred in 50 ml of N,N-dimethylformamide at room temperature for 3 hours. The resulting reaction mixture was poured into 300 ml of water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 3.1 g of (2-ethoxymethoxy-5-(4-trifluoromethylphenyl)phenyl] 2,2,2-trifluoroethyl sulfide (yield 75.6%) as a pale yellow viscous liquid (nD20 1.5213).

Fuente