2-Fluoro-4-iodoaniline → 4-Amino-3-fluorobenzonitrile

HRID 2119439Notes

Reaction equation

HRID 2119439 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]([Cu])#[N:11]>CN(C=O)C.CCOC(C)=O.[Cu]I>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([C:10]#[N:11])=[CH:8][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 1856942-Fluoro-4-iodoanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 27564314-Amino-3-fluorobenzonitrileYield 101.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-4-iodoaniline (5.0 g, 21 mmol) was dissolved in 20 mL dry DMF. To it were added CuCN (3.8 g, 42 mmol) and catalytic amount of CuI (200 mg). The slurry was refluxed for 1 hour. Diluted with EtOAc. Filtered through celite. Concentrated in vacuuo to yield solid 4-amino-3-fluorobenzonitrile (2.9 g, 100%). ES-MS: (M+H)+ 137.

Workup

  1. temperatureThe slurry was refluxed for 1 hour
  2. filtrationFiltered through celite
  3. concentrationConcentrated in vacuuo

Sources & evidence

ORD record
ord-9662c504b39542a38ca8fdfa67f3fb6d
Source dataset
uspto-grants-2004_02
Patent number
US06686368B1

Reaction notes

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