Reaktion #63247

Reaktionsgleichung

2-propyl-3,4dichlorophenol

potassium iodide

1,5-dibromopentane

sodium hydride

→

5-(2-propyl-3,4-dichlorophenoxy)pentyl bromide

Lösungsmittel

water

ethyl acetate

hexamethylphosphoramide

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution was evaporated to dryness
2. 2
   workup.ADDITIONEthyl acetate and water were added to the residue
3. 3
   Sonstigethe layers were separated
4. 4
   WaschenThe ethyl acetate layer was washed
5. 5
   workup.ADDITIONwith dilute acid
6. 6
   Sonstigeto remove residual hexamethylphosphoramide
7. 7
   WaschenThe ethyl acetate was then washed with a saturated sodium chloride solution
8. 8
   Filtrationfiltered through sodium sulfate
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeThe residue was purified by high pressure liquid chromatography
11. 11
    Sonstigeto provide 1.6 g

Vorschrift

To a solution of 3.12 g. of 2-propyl-3,4dichlorophenol in 30 ml. of dry tetrahydrofuran and 30 ml. of dry hexamethylphosphoramide were added 0.72 g. of a 50% sodium hydride dispersion in oil. Two milliliters of 1,5-dibromopentane were then added followed by a catalytic amount of potassium iodide. The reaction was stirred overnight under a nitrogen atmosphere at 60°-70° C. The reaction was then cooled to room temperature, ethyl acetate and water were added, and the solution was evaporated to dryness. Ethyl acetate and water were added to the residue and the layers were separated. The ethyl acetate layer was washed with dilute acid to remove residual hexamethylphosphoramide. The ethyl acetate was then washed with a saturated sodium chloride solution, filtered through sodium sulfate, and evaporated to dryness. The residue was purified by high pressure liquid chromatography to provide 1.6 g. of the desired bromo intermediate. NMR.

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