Reaction #2460307

Reaction equation

1,4-benzene diboronic acid

butyl 4-iodobenzoate

sodium carbonate

1,2-dimethoxyethane

→

dibutyl 4,4′-terphenyl dicarboxylate

Solvents

water

ethanol

water

Dichloromethane

Conditions

Workup

1. 1
   workup.WAITthe sparging was continued for 5 min
2. 2
   OtherThe stirred reaction mixture
3. 3
   Temperatureat reflux under nitrogen for 44 h
4. 4
   Temperaturecooled
5. 5
   OtherThe organic layer was separated
6. 6
   Dryingdried (MgSO4)
7. 7
   Otherto remove residual catalyst
8. 8
   Concentrationconcentrated
9. 9
   OtherThe product was purified by column chromatography
10. 10
    Otherfollowed by recrystallization from heptane
11. 11
    OtherThe product was obtained as white needles, mass

Procedure

Finally, dibutyl 4,4′-terphenyl dicarboxylate (CS-13) was prepared. A mixture of 1,4-benzene diboronic acid (1.00 g, 6.0 mmol), butyl 4-iodobenzoate (4.04 g, 13 mmol), sodium carbonate (1.92 g, 18 mmol), 1,2-dimethoxyethane (25 mL), ethanol (7 mL), and water (10 mL) was deaerated by sparing with nitrogen for 10 min. Dichlorobis(triphenylphosphine)-palladium(II) (0.085 g, 0.12 mmol) was added, and the sparging was continued for 5 min. The stirred reaction mixture was held at reflux under nitrogen for 44 h and then cooled to ambient. Dichloromethane (100 mL) and water (100 mL) were added. The organic layer was separated dried (MgSO4), passed through a short column of silica gel to remove residual catalyst, and concentrated to deposit a crude product. The product was purified by column chromatography followed by recrystallization from heptane and then from acetonitrile. The product was obtained as white needles, mass: 1.45 g (56% of theory). 1H NMR (CDCl3): δ 1.00 (t, 6H), 1.5 (m, 4H), 1.8 (m, 4H), 4.36 (q, 4H), 7.75 (m, 8H), 8.13 (d, 4H).

Source