Reaktion #69667

Reaktionsgleichung

2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester

n-butylamine

→

title compound

Ausbeute 119.5%

2,4-bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester

Ausbeute 119.5%

Lösungsmittel

water

2-propanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with N2 for 5 minutes
2. 2
   Temperaturthe mixture was heated
3. 3
   Temperaturat reflux for 20 h
4. 4
   Temperaturto cool
5. 5
   Extraktionextracted with EtOAc (2×300 mL)
6. 6
   WaschenThe combined organic extracts were washed with 1M aqueous HCl, brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered through a plug of Celite

Vorschrift

A mixture of 2,4-bis-benzyloxy-5-bromo-benzoic acid benzyl ester (10.0 g, 20 mmol), potassium isopropenyl trifluoroborate (4.0 g, 27.2 mmol) and n-butylamine (6.0 mL, 60 mmol) in 2-propanol/water (2:1, 200 mL) was purged with N2 for 5 minutes. To this mixture was added [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) (816 mg, 1.09 mmol) and the mixture was heated at reflux for 20 h. The mixture was allowed to cool to ambient then diluted with water (400 mL) and extracted with EtOAc (2×300 mL). The combined organic extracts were washed with 1M aqueous HCl, brine, dried (MgSO4), filtered through a plug of Celite and the filtrate reduced in vacuo to give the title compound (11.1 g) as a brown gum.

Quelle