Reacción #40267

Ecuación de reacción

6-bromo-1-chloro-2-naphthol

4-pentyl-phenylboric acid

sodium carbonate

toluene ethanol water

→

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

Rendimiento 78.1%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 10 hours
2. 2
   Lavadowashed with 1N HCl(aq) and water
3. 3
   Secadodried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under a reduced pressure
5. 5
   Otroto remove the solvent
6. 6
   OtroThe residue was purified by silica gel column chromatography
7. 7
   Otrodried under a reduced pressure

Procedimiento

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).

Fuente