Reaktion #360566

Reaktionsgleichung

4-bromo-3,5-dimethylphenol

potassium iodide

potassium carbonate

2-chloroethyl ethyl ether

→

title compound

Ausbeute 98.0%

2-bromo-5-(2-ethoxyethoxy)-1,3-dimethylbenzene

Ausbeute 98.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 70° C. for 2 days
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was partitioned between ethyl acetate and water
5. 5
   WaschenThe organic layer was washed with saturated brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1)

Vorschrift

To a solution of 4-bromo-3,5-dimethylphenol (12 g, 59.7 mmol), potassium iodide (1.5 g, 9.0 mmol) and potassium carbonate (9.9 g, 71.6 mmol) in N,N-dimethylformamide (80 mL) was added 2-chloroethyl ethyl ether (9.7 g, 89.3 mmol) at room temperature with stirring and the mixture was stirred at 70° C. for 2 days. The reaction mixture was cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=19/1) to give the title compound (15.9 g, yield 98%) as a yellow oil.

Quelle