4-Chloro-5-fluoro-2-iodoaniline → 2-Amino-5-chloro-4-fluorobenzonitrile
Reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[C:4](I)[CH:3]=1.[Cu][C:12]#[N:13]>CC(N(C)C)=O>[NH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[CH:3][C:4]=1[C:12]#[N:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-chloro-5-fluoro-2-iodo-phenylamine (2.5 g, 9.21 mmol) and copper (I) cyanide (1.65 g, 18.4 mmol) in DMA (45 ml) was heated to 130° C. overnight. Most of the DMA was removed under reduced pressure and the remaining residue was diluted with EtOAc and dichloromethane. The slurry was filtered and the filter cake was washed with dichloromethane and EtOAc. The filtrate was concentrated and the remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-85:15) to afford the title compound (1232 mg, 78%) as light red solid. MS (ESI): 169.2 (M−H)−.