تفاعل #52920

معادلة التفاعل

BBr3

N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

→

N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester

المردود 50.4%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred for 3 h
2. 2
   أخرىquenched with EtOH
3. 3
   أخرىThe solvent was removed
4. 4
   غسيلThe solution was washed with satd
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىevaporated
7. 7
   أخرىThe residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1)

الإجراء التجريبي

BBr3 (1 mL, 1M in CH2Cl2) was added to a CH2Cl2 (10 mL) solution of N-(2,6-dichlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (0.215 g) at 0° C. with stirring and the solution was slowly warmed to room temperature. The mixture was stirred for 3 h and quenched with EtOH. The solvent was removed and the residue was taken up in EtOAc. The solution was washed with satd. NaHCO3 followed by brine, dried (MgSO4) and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: hexanes/EtOAc 2:1) to yield 0.105 g of N-(2,6-dichlorobenzoyl)-4-(2-hydroxyphenyl)-L-phenylalanine methyl ester. ESMS: m/z 444 (MH+).

المصدر