Reacción #2460311

Ecuación de reacción

butyl 4′-bromobiphenyl-3-carboxylate

4-trifluoromethylbenzene boronic acid

potassium carbonate

18-crown-6

toluene

toluene

→

3-butoxycarbonyl-4′-trifluoromethyl-p-terphenyl

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 44 h
4. 4
   workup.ADDITIONwere added
5. 5
   OtroThe organic layer was separated
6. 6
   Lavadowashed with water and with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Concentraciónconcentrated
9. 9
   OtroThe product was purified by column chromatography
10. 10
    Otrofollowed by recrystallization from heptane
11. 11
    Otroto provide 0.96 g (45% of theory) of a white powder

Procedimiento

Finally, 3-butoxycarbonyl-4′-trifluoromethyl-p-terphenyl (CS-18) was prepared. A mixture of butyl 4′-bromobiphenyl-3-carboxylate (1.80 g, 5.4 mmol), 4-trifluoromethylbenzene boronic acid (1.08 g, 5.7 mmol), potassium carbonate (2.24 g, 16 mmol), toluene (30 mL), and 18-crown-6 (20 mg) was deaerated by sparging with nitrogen for 10 min. Tetrakis(triphenylphosphine)-palladium(0) (0.12 g, 0.11 mmol) was added, and the mixture was heated at reflux for 44 h. Additional tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.10 mmol) was added, and the reaction was continued for 24 h. The mixture was cooled to ambient, and toluene (30 mL) and water (30 mL) were added. The organic layer was separated, washed with water and with brine, dried (MgSO4), passed through short column of silica gel, and concentrated to deposit a gold solid. The product was purified by column chromatography followed by recrystallization from heptane to provide 0.96 g (45% 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), 7.51 (t, 1H), 7.7 (m, 8H), 7.80 (d, 1H), 8.03 (d, 1H), 8.30 (s, 1H).

Fuente