Реакция #59033

Уравнение реакции

2-(4-bromo-2,6-dimethylphenoxy)ethanol

4-carboxyphenylboronic acid

cesium fluoride

1,4-dioxane

→

title compound

Выход 38.2%

4′-(2-Hydroxyethoxy}-3′,5′-dimethylbiphenyl-4-carboxylic acid

Выход 38.2%

Растворители

water

ethanol

ethyl acetate

Water

Условия реакции

Обработка

1. 1
   ДругоеThe organic layer was separated
2. 2
   Промывкаwashed with water and brine
3. 3
   Сушкаdried over anhydrous magnesium sulfate
4. 4
   ДругоеThe solvent was evaporated under reduced pressure
5. 5
   Другоеthe residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/1-2/1)

Методика

A mixture of 2-(4-bromo-2,6-dimethylphenoxy)ethanol (0.65 g), 4-carboxyphenylboronic acid (0.87 g), tetrakis(triphenylphosphine)palladium(0) (0.15 g), cesium fluoride (2.40 g), 1,4-dioxane (7.5 mL), ethanol (2.5 mL) and water (1.5 mL) was stirred at 90° C. overnight under an atmosphere of argon. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/1-2/1) to afford the title compound (0.29 g).

Источник