Reacción #586124

ord-0fbc315e828d4f1596636d7f04b90a6e

Ecuación de reacción

O
water
Cc1ccc(-c2c(Cl)cc(C(F)(F)F)cc2Cl)cc1Sc1cc(-c2c(Cl)cc(C(F)(F)F)cc2Cl)ccc1C
1,1′-thiodi-[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzene]
O=S([O-])CO.[Na+]
Rongalite
CC(C)I
isopropyl iodide
Cc1ccc(-c2c(Cl)cc(C(F)(F)F)cc2Cl)cc1SC(C)C
[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylphenyl] isopropyl sulfide
Rendimiento 75.3%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

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 (4.9 mmol) of 1,1′-thiodi-[5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzene], 3.0 g (19.5 mmol) of Rongalite and 3.0 g (17.6 mmol) of isopropyl iodide were stirred in 30 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 1.4 g of [5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylphenyl] isopropyl sulfide (yield 38.0%) as a yellow dough (nD20 1.5462).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07767626B2uspto-grants-2010_08