Reacción #43903

Ecuación de reacción

4-bromo-3,5-dimethylphenol

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

Tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

Rendimiento 86.6%

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

Rendimiento 86.6%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente