反応 #69667

反応方程式

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

n-butylamine

→

title compound

収率 119.5%

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

収率 119.5%

溶媒

water

2-propanol water

反応条件

後処理

1. 1
   その他was purged with N2 for 5 minutes
2. 2
   温度the mixture was heated
3. 3
   温度at reflux for 20 h
4. 4
   温度to cool
5. 5
   抽出extracted with EtOAc (2×300 mL)
6. 6
   洗浄The combined organic extracts were washed with 1M aqueous HCl, brine
7. 7
   乾燥dried (MgSO4)
8. 8
   ろ過filtered through a plug of Celite

実験手順

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.

出典