Reacción #8497

Ecuación de reacción

1,3,5-trichlorobenzene

sodium hydroxide

tert-butylmercaptan

→

( 4 )

Rendimiento 19.0%

3,5-Dichlorophenyl-tert-butylsulfide

Rendimiento 19.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was refluxed at 140° C. for 6.5 hours
2. 2
   Extracciónextracted with ethylacetate
3. 3
   Lavadowashed with water
4. 4
   Secadodried over sodium sulphate
5. 5
   Filtraciónfiltrated
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe obtained residue was chromatographed twice on silica gel (SiO2 15 g, elution: n-hexane)

Procedimiento

To a solution of 4N sodium hydroxide (0.8 ml) was added tert-butylmercaptan (0.406 ml). The mixture was stirred for 15 minutes at room temperature. Tetra n-butylammonium bromide (322 mg, 1 mmol) and 1,3,5-trichlorobenzene (1) (1.8 g, 10 mmol) were added thereto. The reaction mixture was refluxed at 140° C. for 6.5 hours. The reaction mixture was poured into ice-water, extracted with ethylacetate, washed with water, dried over sodium sulphate, filtrated and concentrated under reduced pressure. The obtained residue was chromatographed twice on silica gel (SiO2 15 g, elution: n-hexane) to yield the objective (4) (138 mg). Yield 19%.

Fuente