Reacción #712882

Ecuación de reacción

potassium carbonate

4-Bromo-2,6-dimethylphenol

toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester

water

Intermediate 10

toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester

→

title compound

Rendimiento 70.0%

4-(4-Bromo-2,6-dimethyl-phenoxy)-2-methyl-butan-2-ol

Rendimiento 70.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is cooled
2. 2
   Extracciónextracted with diethyl ether
3. 3
   OtroThe organic phase is dried
4. 4
   Otrothe solvent removed
5. 5
   OtroThe residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane)

Procedimiento

4-Bromo-2,6-dimethylphenol (2.00 g, 9.95 mmol), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (Intermediate 10, 2.83 g, 10.9 mmol) and potassium carbonate (1.01 g, 10.9 mmol) are combined in N,N-dimethylformamide (50 mL) and heated at 80° C. for 24 hours. The mixture is cooled, poured into water and extracted with diethyl ether. The organic phase is dried and the solvent removed. The residue is purified by flash chromatography (0-50% ethyl acetate in cyclohexane) to give the title compound (Yield 2.00 g). GC (METHOD 1): tR=11.26 min; Mass spectrum (EI+): m/z=286/288 [M]+.

Fuente