Reaction #40267

Reaction equation

6-bromo-1-chloro-2-naphthol

4-pentyl-phenylboric acid

sodium carbonate

toluene ethanol water

→

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

Yield 78.1%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturerefluxed for 10 hours
2. 2
   Washwashed with 1N HCl(aq) and water
3. 3
   Dryingdried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under a reduced pressure
5. 5
   Otherto remove the solvent
6. 6
   OtherThe residue was purified by silica gel column chromatography
7. 7
   Otherdried under a reduced pressure

Procedure

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