反応 #2460311

反応方程式

butyl 4′-bromobiphenyl-3-carboxylate

4-trifluoromethylbenzene boronic acid

potassium carbonate

18-crown-6

toluene

toluene

→

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

溶媒

water

反応条件

後処理

1. 1
   その他by sparging with nitrogen for 10 min
2. 2
   温度the mixture was heated
3. 3
   温度at reflux for 44 h
4. 4
   workup.ADDITIONwere added
5. 5
   その他The organic layer was separated
6. 6
   洗浄washed with water and with brine
7. 7
   乾燥dried (MgSO4)
8. 8
   濃縮concentrated
9. 9
   その他The product was purified by column chromatography
10. 10
    その他followed by recrystallization from heptane
11. 11
    その他to provide 0.96 g (45% of theory) of a white powder

実験手順

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).

出典