{3-[(3-Chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid → 3-Chloro-5-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]benzonitrile
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:24])=[C:13]([CH2:20]C(O)=O)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:10][C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([CH3:20])[C:12]=2[F:24])[CH:3]=1)[C:8]#[N:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The crude {3-[(3-chloro-5-cyanophenyl)oxy]-2-fluoro-4-nitrophenyl}acetic acid was dissolved in CH3CN (50 mL) and Cu2O (0.65 g, 4.5 mmol) was added. A condenser was attached and the heterogeneous mixture was heated to reflux for 2 h. The reaction mixture was cooled to RT, filtered through Celite and the solvent evaporated. Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (6.0 g, 87%), which solidified upon standing. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.98 (dd, 1H), 7.81 (d, 1H), 7.60 (d, 2H), 7.52 (t, 1H), 2.37 (d, 3H).