Reacción #324638

Ecuación de reacción

2,2-dimethyloxirane

4-bromo-3,5-dimethylphenol

K2CO3

→

title compound

1-(4-Bromo-3,5-dimethylphenoxy)-2-methylpropan-2-ol

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe vial is sealed
2. 2
   Temperaturathe mixture is heated for 48 hours to 120° C
3. 3
   Otrois partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
4. 4
   ExtracciónThe aqueous phase is extracted twice with ethyl acetate
5. 5
   Secadothe combined organic phases are dried (MgSO4)
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→50:50)

Procedimiento

In a microwave vial 2,2-dimethyloxirane (2.2 g) is added to a suspension of 4-bromo-3,5-dimethylphenol and K2CO3 (11 g) in N,N-dimethylformamide (6 mL). The vial is sealed and the mixture is heated for 48 hours to 120° C. After cooling to room temperature the mixture is partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→50:50) to give the title compound. Yield: 2.9 g; LC (method 4): tR=1.76 min; Mass spectrum (ESI+): m/z=273 [M+H]+.

Fuente