반응 #1552083

반응 방정식

1-bromo-4-butylbenzene

4-(methoxycarbonyl)phenylboronic acid

Na2CO3

N2

→

methyl 4-(4-butylphenyl)benzoate

수율 86.0%

용매

toluene EtOH

반응 조건

후처리

1. 1
   기타The resulting mixture was degassed with N2 three times
2. 2
   온도heated
3. 3
   온도to reflux for 5 hrs
4. 4
   기타toluene and EtOH was removed under vacuum
5. 5
   추출The residue was extracted with EA (30 mL×3)
6. 6
   세척The combined organic layers were washed with brine
7. 7
   건조dried with Na2SO4
8. 8
   기타The solvent was removed
9. 9
   기타to give the crude product
10. 10
    기타The crude product was purified by column chromatography on silica gel
11. 11
    세척eluted with PE, PE
12. 12
    기타The solvent was removed

실험 절차

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.

출처