Reacción #324633

Ecuación de reacción

4-bromo-3,5-dimethylphenol

Cs2CO3

tetrahydro-2H-pyran-4-yl methanesulfonate

→

title compound

4-(4-Bromo-3,5-dimethylphenoxy)tetrahydro-2H-pyran

Disolventes

N-methyl-pyrrolidone

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature the mixture
2. 2
   Otrois partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
3. 3
   ExtracciónThe aqueous phase is extracted with ethyl acetate
4. 4
   Secadothe combined organic phases are dried (MgSO4)
5. 5
   OtroThe solvents are evaporated
6. 6
   Otrothe residue is purified by HPLC on reversed phase

Procedimiento

To a solution of 4-bromo-3,5-dimethylphenol (3 g) in N-methyl-pyrrolidone (10 mL) is slowly added Cs2CO3 (9.7 g) and tetrahydro-2H-pyran-4-yl methanesulfonate (5.4 g). The mixture is heated for 3 hours at 140° C. After cooling to room temperature the mixture is partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (MgSO4). The solvents are evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 1.2 g; LC (method 4): tR=1.83 min.

Fuente