Реакция #1605858

Уравнение реакции

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

4-bromo-3,5-dimethylphenol

ethyl acetate

potassium carbonate

→

title compound

Выход 91.0%

4-(4-bromo-3,5-dimethylphenoxy)-2-methylbutan-2-ol

Выход 91.0%

Растворители

water

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Экстракцияthe mixture was extracted with ethyl acetate
2. 2
   ПромывкаThe organic phase was successively washed with water (50 mL) and brine (50 mL)
3. 3
   Сушкаdried over anhydrous sodium sulfate
4. 4
   workup.DISTILLATIONFrom the organic phase, the solvent was distilled off under reduced pressure
5. 5
   Другоеthe resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=80:20 to 70:30)
6. 6
   workup.DISTILLATIONFrom the eluted solution, the solvent was distilled off under reduced pressure

Методика

A mixed solution of 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (4.24 g) synthesized in accordance with the method described in [WO 2009/067613 pamphlet, Example 308], 4-bromo-3,5-dimethylphenol (3.0 g), and potassium carbonate (3.09 g) in N,N-dimethylformamide (15 mL) was stirred at 80° C. for 3 hours. To the reaction mixture, ethyl acetate (200 mL) and water (100 mL) were added and the mixture was extracted with ethyl acetate. The organic phase was successively washed with water (50 mL) and brine (50 mL) and then dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=80:20 to 70:30). From the eluted solution, the solvent was distilled off under reduced pressure to give the title compound (3.9 g).

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