Reacción #663849

Ecuación de reacción

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

4-bromo-3,5-dimethylphenol

ethyl acetate

potassium carbonate

→

title compound

Rendimiento 91.0%

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

Rendimiento 91.0%

Disolventes

water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate
2. 2
   LavadoThe organic phase was successively washed with water (50 mL) and brine (50 mL)
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   OtroFrom the organic phase, the solvent was removed by evaporation under reduced pressure
5. 5
   Otrothe resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=80:20 to 70:30)
6. 6
   OtroFrom the eluted solution, the solvent was removed by evaporation under reduced pressure

Procedimiento

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 removed by evaporation 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 removed by evaporation under reduced pressure to give the title compound (3.9 g).

Fuente