Réaction #712882

Équation de réaction

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

Rendement 70.0%

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

Rendement 70.0%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source