2-Bromo-4-trifluoromethylaniline → 4-Amino-3-cyanobenzotrifluoride

HRID 131327

Reaction equation

HRID 131327 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[NH2:15]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:15][C:6]1[CH:5]=[CH:10][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:8][C:7]=1[C:2]#[N:3]

Participants

5

Reactant 2

HCID 938992-Bromo-4-trifluoromethylanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 126273614-Amino-3-cyanobenzotrifluorideYield 47%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a mixture of copper (I) cyanide (2.24 g, 25.00 mmol) and 2-bromo-4-trifluoromethyl-phenylamine (5.0 g, 20.83 mmol from Avocado) in 1-methyl-2-pyrrolidinone (20 ml) to 195° C. for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and wash the dark solution twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue via flash chromatography eluting with a step gradient starting with hexanes and going to 70% hexanes with 30% ethyl acetate to obtain 1.821 g (9.78 mmol, 47% yield) the title compound as a green amorphous solid: Mass Spectrum (m/e): 187(M+1).

Workup

  1. temperatureHeat
  2. washwash the dark solution twice with 28% aqueous ammonium hydroxide
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the residue via flash chromatography
  7. washeluting with a step gradient

Sources & evidence

ORD record
ord-4be442a3741e4283909eab11721f7e9a
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Linked notes

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