Reaction #2460309

Reaction equation

butyl 4-iodobenzoate

4-trifluoromethylbenzene boronic acid

potassium carbonate

toluene

→

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

Solvents

water

Conditions

Workup

1. 1
   Otherby sparging with nitrogen for 10 min
2. 2
   Temperaturethe mixture was heated
3. 3
   Temperatureat reflux for 3 h
4. 4
   Temperaturecooled
5. 5
   OtherThe organic layer was separated
6. 6
   Washwashed with brine
7. 7
   Dryingdried (MgSO4)
8. 8
   Concentrationconcentrated
9. 9
   OtherThe product was purified by recrystallization from aqueous isopropanol
10. 10
    Otherto provide 1.03 g (28% of theory) of a white powder

Procedure

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).

Source