Methanol → 3-Amino-3-(3-bromo-5-fluorophenyl)propionic acid methyl ester
Reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([Br:14])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([Br:14])[CH:8]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
1.59 g (6.05 mmol) 3-amino-3-(3-bromo-5-fluorophenyl)propionic acid were suspended in 24.5 ml methanol and the mixture cooled to 0° C. 0.66 ml (9.08 mmol) thionyl chloride were slowly added. The mixture was stirred at room temperature for 20 hours and concentrated. The residue was treated with saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The organic part was dried with sodium sulfate and concentrated. Chromatography over 10 g silica gel (dichloromethane/ethanol 100/0-95/5-90/10) gave 1.55 g (93%) 3-amino-3-(3-bromo-5-fluorophenyl)propionic acid methyl ester.