Reaktion #732497

Reaktionsgleichung

6-bromo-1-chloro-2-naphthol

4-pentylphenylboronic acid

sodium carbonate

→

6-(4-pentylphenyl)-1-chloro-2-naphthol

Ausbeute 72.1%

Lösungsmittel

toluene

water

ethanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 10 hours
2. 2
   WaschenThe reaction mixture was washed with 1N hydrochloric acid and water
3. 3
   Trocknenafter drying over magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   SonstigeThe resulting residue was purified by silica gel column chromatography with toluene as a developing solvent

Vorschrift

55 g of 6-bromo-1-chloro-2-naphthol (S1-2), 12.3 g of 4-pentylphenylboronic acid (S1-3), 1.0 g of tetrakistriphenylphosphine palladium, 13.6 g of sodium carbonate and 100 mL of a mixed solvent of toluene, ethanol and water (3/3/1) were added to a reactor under a nitrogen atmosphere and refluxed for 10 hours. The reaction mixture was cooled to room temperature, and toluene was added thereto. The reaction mixture was washed with 1N hydrochloric acid and water, and after drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography with toluene as a developing solvent to provide 15 g of 6-(4-pentylphenyl)-1-chloro-2-naphthol (S1-4).

Quelle