反应 #2460311

反应方程式

butyl 4′-bromobiphenyl-3-carboxylate

4-trifluoromethylbenzene boronic acid

potassium carbonate

18-crown-6

toluene

toluene

→

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

溶剂

water

反应条件

后处理

1. 1
   其他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
   其他The organic layer was separated
6. 6
   洗涤washed with water and with brine
7. 7
   干燥dried (MgSO4)
8. 8
   浓缩concentrated
9. 9
   其他The product was purified by column chromatography
10. 10
    其他followed by recrystallization from heptane
11. 11
    其他to provide 0.96 g (45% of theory) of a white powder

实验过程

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).

来源