Réaction #40267

Équation de réaction

6-bromo-1-chloro-2-naphthol

4-pentyl-phenylboric acid

sodium carbonate

toluene ethanol water

→

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

Rendement 78.1%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 10 hours
2. 2
   Lavagewashed with 1N HCl(aq) and water
3. 3
   Séchagedried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under a reduced pressure
5. 5
   Autreto remove the solvent
6. 6
   AutreThe residue was purified by silica gel column chromatography
7. 7
   Autredried under a reduced pressure

Mode opératoire

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).

Source