Methyl 2-bromo-3-(4-fluorophenyl)propanoate → Methyl 3-(4-fluorophenyl)propanoate
Reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4]>C(O)(=O)C.[Zn]>[F:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Crude methyl 2-bromo-3-(4-fluorophenyl)propionate in acetic acid (330 ml) was stirred and treated with zinc dust (32.75 g) in portions over 30 minutes. The mixture was stirred for an additional 30 minutes and filtered, and the filter cake was washed with acetic acid. After the filtrate was evaporated the residue was partitioned between methylene chloride and water to give crude methyl 3-(4-fluorophenyl)propionate, which was refluxed with aqueous sodium hydroxide (400 ml, 10%) for 2 hrs, cooled, treated with decolorizing carbon, and filtered. The filtrate was acidified with 5 N HCl and filtered. The filter cake was washed extensively with water to give 3-(4-fluorophenyl)propionic acid (20.0 g) as colourless crystals, mp 90° C.