[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][C:7]=1I.N#N.[CH3:17][N:18](C)C=O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:17]([C:7]1[CH:6]=[CH:5][C:4]([CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:3][C:2]=1[F:1])#[N:18]Methyl 2-(3-fluoro-4-iodophenyl)propanoate, tetrakis(triphenylphosphine) palladium(0) and zinc cyanide are placed in dimethylformamide and charged with N2. The reaction mixture was stirred at 120° C. for 15 h and cooled to room temperature. The reaction mixture is filtered by celite packed filter, washed with ethyl acetate. After concentrate solvent, residue is purified on a silica gel column using ethylacetate-hexane as solvent system to give methyl 2-(4-cyano-3-fluorophenyl)propanoate.
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