Реакция #324638

Уравнение реакции

2,2-dimethyloxirane

4-bromo-3,5-dimethylphenol

K2CO3

→

title compound

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

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

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

Методика

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]+.

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