反応 #40267

反応方程式

6-bromo-1-chloro-2-naphthol

4-pentyl-phenylboric acid

sodium carbonate

toluene ethanol water

→

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

収率 78.1%

溶媒

toluene

反応条件

後処理

1. 1
   温度refluxed for 10 hours
2. 2
   洗浄washed with 1N HCl(aq) and water
3. 3
   乾燥dried over magnesium sulfate
4. 4
   workup.DISTILLATIONdistilled under a reduced pressure
5. 5
   その他to remove the solvent
6. 6
   その他The residue was purified by silica gel column chromatography
7. 7
   その他dried under a reduced pressure

実験手順

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).

出典