Reaktion #40267

Reaktionsgleichung

6-bromo-1-chloro-2-naphthol

4-pentyl-phenylboric acid

sodium carbonate

toluene ethanol water

→

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

Ausbeute 78.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 10 hours
2. 2
   Waschenwashed with 1N HCl(aq) and water
3. 3
   Trocknendried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under a reduced pressure
5. 5
   Sonstigeto remove the solvent
6. 6
   SonstigeThe residue was purified by silica gel column chromatography
7. 7
   Sonstigedried under a reduced pressure

Vorschrift

At first, 55 g of 6-bromo-1-chloro-2-naphthol (S1-2), 12.3 g of 4-pentyl-phenylboric acid (S1-3), 1.0 g of tetrakis(triphenylphosphine) palladium, 13.6 g of sodium carbonate and 100 ml of a mixed solvent of toluene/ethanol/water=3/3/1 were added to a reactor in nitrogen atmosphere and refluxed for 10 hours. The reaction solution was cooled to room temperature, added with toluene, and then washed with 1N HCl(aq) and water, dried over magnesium sulfate and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using toluene as an eluting solvent, and then dried under a reduced pressure to obtain 15 g of 6-(4-pentylphenyl)-1-chloro-2-naphthol (S1-4).

Quelle