Reacción #66498

Ecuación de reacción

5-bromo-2-methylsulfanylpyrimidine

Oxone

sodium hydroxide

→

sulfone

Rendimiento 80.0%

5-bromo-2-methylsulfonylpyrimidine

Rendimiento 80.0%

Disolventes

Water

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONin an alternating addition mode
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   Extracciónthe mixture was extracted with ethyl acetate (2×500 mL)
4. 4
   workup.ADDITIONThe aqueous layer was adjusted to pH 7 by addition of aq. sodium hydroxide
5. 5
   Extracciónwas again extracted with ethyl acetate
6. 6
   SecadoThe combined organic layers were dried over MgSO4
7. 7
   Otroevaporated

Procedimiento

To a solution of 5-bromo-2-methylsulfanylpyrimidine (10.0 g, 48.8 mmol) in methanol (195 mL) were added a solution of Oxone® (94.6 g, 154 mmol, 3.16 eq) in water (500 mL and aq. 4 N sodium hydroxide (40 mL, 160 mmol, 3.28 eq.) portionwise and in an alternating addition mode to maintain pH between 2 and 3 at a temperature of 0° C. After complete addition, the mixture was allowed to stir for 2 h at room temperature. Water (500 mL) was added, and the mixture was extracted with ethyl acetate (2×500 mL). The aqueous layer was adjusted to pH 7 by addition of aq. sodium hydroxide, and was again extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and evaporated to give 9.23 g (80% yield) of the desired sulfone which was used without further purification.

Fuente