Реакция #324633

Уравнение реакции

4-bromo-3,5-dimethylphenol

Cs2CO3

tetrahydro-2H-pyran-4-yl methanesulfonate

→

title compound

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

Растворители

N-methyl-pyrrolidone

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling to room temperature the mixture
2. 2
   Другоеis partitioned between saturated aqueous Na2CO3 solution and ethyl acetate
3. 3
   ЭкстракцияThe aqueous phase is extracted with ethyl acetate
4. 4
   Сушкаthe combined organic phases are dried (MgSO4)
5. 5
   ДругоеThe solvents are evaporated
6. 6
   Другоеthe residue is purified by HPLC on reversed phase

Методика

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.

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