تفاعل #69667

معادلة التفاعل

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

n-butylamine

→

title compound

المردود 119.5%

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

المردود 119.5%

المذيبات

water

2-propanol water

ظروف التفاعل

المعالجة

1. 1
   أخرىwas purged with N2 for 5 minutes
2. 2
   درجة الحرارةthe mixture was heated
3. 3
   درجة الحرارةat reflux for 20 h
4. 4
   درجة الحرارةto cool
5. 5
   استخلاصextracted with EtOAc (2×300 mL)
6. 6
   غسيلThe combined organic extracts were washed with 1M aqueous HCl, brine
7. 7
   تجفيفdried (MgSO4)
8. 8
   ترشيحfiltered through a plug of Celite

الإجراء التجريبي

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.

المصدر