Reacción #2460309

Ecuación de reacción

butyl 4-iodobenzoate

4-trifluoromethylbenzene boronic acid

potassium carbonate

toluene

→

butyl 4′-(trifluoromethyl)biphenyl-4-carboxylate

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroby sparging with nitrogen for 10 min
2. 2
   Temperaturathe mixture was heated
3. 3
   Temperaturaat reflux for 3 h
4. 4
   Temperaturacooled
5. 5
   OtroThe organic layer was separated
6. 6
   Lavadowashed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe product was purified by recrystallization from aqueous isopropanol
10. 10
    Otroto provide 1.03 g (28% of theory) of a white powder

Procedimiento

A mixture of butyl 4-iodobenzoate (3.5 g, 11 mmol), 4-trifluoromethylbenzene boronic acid (2.30 g, 12 mmol), potassium carbonate (4.77 g, 35 mmol), toluene (40 mL), and water (20 mL) was deaerated by sparging with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium(0) (0.27 g, 0.23 mmol) was added, and the mixture was heated at reflux for 3 h and then cooled to ambient. The organic layer was separated, washed with brine, dried (MgSO4), passed through short column of silica gel, and concentrated to deposit a gold solid. The product was purified by recrystallization from aqueous isopropanol to provide 1.03 g (28% of theory) of a white powder. 1H NMR (CDCl3): δ 1.00 (t, 3H), 1.5 (m, 2H), 1.8 (m, 2H), 4.36 (t, 2H), 7.66 (d, 2H), 7.72 (s, 4H), 8.14 (d, 2H).

Fuente