Реакция #43903

Уравнение реакции

4-bromo-3,5-dimethylphenol

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

Tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

Выход 86.6%

4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-thiopyran

Выход 86.6%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was further stirred for 1.5 hr
2. 2
   КонцентрированиеThe reaction mixture was concentrated under reduced pressure
3. 3
   Другоеthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

Методика

To a solution of 4-bromo-3,5-dimethylphenol (0.201 g, 1.00 mmol), tetrahydro-2H-thiopyran-4-ol (0.130 g, 1.10 mmol) and triphenylphosphine (0.341 g, 1.30 mmol) in tetrahydrofuran (5 mL) was added diethyl azodicarboxylate (40% solution in toluene, 0.591 mL, 1.30 mmol), and the mixture was stirred at room temperature for 1.5 hr. Tetrahydro-2H-thiopyran-4-ol (0.0591 g, 0.500 mmol), triphenylphosphine (0.157 g, 0.600 mmol) and diethyl azodicarboxylate (40% solution in toluene, 0.272 mL, 0.600 mmol) were added, and the mixture was further stirred for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (0.261 g, yield 86%) as colorless crystals.

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