Réaction #1552083

Équation de réaction

1-bromo-4-butylbenzene

4-(methoxycarbonyl)phenylboronic acid

Na2CO3

N2

→

methyl 4-(4-butylphenyl)benzoate

Rendement 86.0%

Solvants

toluene EtOH

Conditions de réaction

Traitement

1. 1
   AutreThe resulting mixture was degassed with N2 three times
2. 2
   Températureheated
3. 3
   Températureto reflux for 5 hrs
4. 4
   Autretoluene and EtOH was removed under vacuum
5. 5
   ExtractionThe residue was extracted with EA (30 mL×3)
6. 6
   LavageThe combined organic layers were washed with brine
7. 7
   Séchagedried with Na2SO4
8. 8
   AutreThe solvent was removed
9. 9
   Autreto give the crude product
10. 10
    AutreThe crude product was purified by column chromatography on silica gel
11. 11
    Lavageeluted with PE, PE
12. 12
    AutreThe solvent was removed

Mode opératoire

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.

Source