反応 #1552083

反応方程式

1-bromo-4-butylbenzene

4-(methoxycarbonyl)phenylboronic acid

Na2CO3

N2

→

methyl 4-(4-butylphenyl)benzoate

収率 86.0%

溶媒

toluene EtOH

反応条件

後処理

1. 1
   その他The resulting mixture was degassed with N2 three times
2. 2
   温度heated
3. 3
   温度to reflux for 5 hrs
4. 4
   その他toluene and EtOH was removed under vacuum
5. 5
   抽出The residue was extracted with EA (30 mL×3)
6. 6
   洗浄The combined organic layers were washed with brine
7. 7
   乾燥dried with Na2SO4
8. 8
   その他The solvent was removed
9. 9
   その他to give the crude product
10. 10
    その他The crude product was purified by column chromatography on silica gel
11. 11
    洗浄eluted with PE, PE
12. 12
    その他The solvent was removed

実験手順

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.

出典