Реакция #1552083

Уравнение реакции

1-bromo-4-butylbenzene

4-(methoxycarbonyl)phenylboronic acid

Na2CO3

N2

→

methyl 4-(4-butylphenyl)benzoate

Выход 86.0%

Растворители

toluene EtOH

Условия реакции

Обработка

1. 1
   ДругоеThe resulting mixture was degassed with N2 three times
2. 2
   Температураheated
3. 3
   Температураto reflux for 5 hrs
4. 4
   Другоеtoluene and EtOH was removed under vacuum
5. 5
   ЭкстракцияThe residue was extracted with EA (30 mL×3)
6. 6
   ПромывкаThe combined organic layers were washed with brine
7. 7
   Сушкаdried with Na2SO4
8. 8
   ДругоеThe solvent was removed
9. 9
   Другоеto give the crude product
10. 10
    ДругоеThe crude product was purified by column chromatography on silica gel
11. 11
    Промывкаeluted with PE, PE
12. 12
    ДругоеThe solvent was removed

Методика

A solution of 1-bromo-4-butylbenzene (100 g, 0.472 mol), 4-(methoxycarbonyl)phenylboronic acid (82.0 g, 0.456 mol), 2 M Na2CO3 (150 g, 1.42 mol) in toluene/EtOH (900 mL/300 mL) was degassed with N2 three times, then Pd(PPh3)4 (27.2 g, 23.6 mmol) was added. The resulting mixture was degassed with N2 three times and then heated to reflux for 5 hrs. After TLC showed the reaction was complete, toluene and EtOH was removed under vacuum. The residue was extracted with EA (30 mL×3). The combined organic layers were washed with brine, dried with Na2SO4. The solvent was removed to give the crude product. The crude product was purified by column chromatography on silica gel eluted with PE, PE:EA (150:1). The solvent was removed to give methyl 4-(4-butylphenyl)benzoate (105 g, yield: 86.0%), as a white solid.

Источник