Réaction #663849

Équation de réaction

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

4-bromo-3,5-dimethylphenol

ethyl acetate

potassium carbonate

→

title compound

Rendement 91.0%

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

Rendement 91.0%

Solvants

water

N,N-dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source