Hydrochloric Acid → 4-Amino-3-fluorobenzonitrile

HRID 2244971Notes

Reaction equation

HRID 2244971 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].CCOC(C)=O.Cl>CN(C=O)C>[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 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 1856942-Fluoro-4-iodoanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 27564314-Amino-3-fluorobenzonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-fluoro-4-iodoaniline (10.0 g, 42.2 mmol) and CuCN (7.56 g, 84.4 mmol) in DMF (40 mL) was heated at reflux for 5 h. After being cooled down, EtOAc and 1N HCl were added. The mixture was filtered through celite. The organic phase was separated, washed sequentially with 1N HCl and brine. It was then dried over MgSO4, concentrated in vacuo to give a brown solid (5.69 g), which was pure enough for the next step. MS 137.1 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperatureAfter being cooled down
  4. filtrationThe mixture was filtered through celite
  5. customThe organic phase was separated
  6. washwashed sequentially with 1N HCl and brine
  7. dry with materialIt was then dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f08b3066020c4b6583afb268ca0fc084
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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