4-Chloro-5-fluoro-2-iodoaniline → 2-Amino-5-chloro-4-fluorobenzonitrile

HRID 1497242Notes

Reaction equation

HRID 1497242 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

HCID 575389634-Chloro-5-fluoro-2-iodoanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 584757642-Amino-5-chloro-4-fluorobenzonitrileYield 78.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

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)−.

Workup

  1. customMost of the DMA was removed under reduced pressure
  2. additionthe remaining residue was diluted with EtOAc and dichloromethane
  3. filtrationThe slurry was filtered
  4. washthe filter cake was washed with dichloromethane and EtOAc
  5. concentrationThe filtrate was concentrated
  6. customthe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-85:15)

Sources & evidence

ORD record
ord-fde37300bbb240708b380f3fb9459157
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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