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

HRID 471552

Reaction equation

HRID 471552 reaction equation
Br[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cu](C#N)[C:14]#[N:15]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:2]=1[C:14]#[N:15]

Participants

5

Reactant 2

HCID 938992-Bromo-4-trifluoromethylanilineHCID 178418260HCID 178418260, compound

Product 1

HCID 126273614-Amino-3-cyanobenzotrifluoride

Reagents, catalysts & solvents 2

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

Procedure

In a 20 mL microwave vial, 2-bromo-4-(trifluoromethyl)aniline (238 mg, 1 mmol) and copper cyanide (90 mg, 1 mmol) were dissolved in N-methylpyrrolidone (NMP) (10 mL). The reaction was placed in a microwave reactor for 5 minutes at 200° C. The crude was dissolved in ethyl acetate and the precipitate was removed by filtration. The clear solution was washed with water. The organic layer was collected, dried over sodium sulfate, and evaporated under vacuum. The residue was purified by Varia HPLC (10% acetonitrile/water) to give the title compound.

Workup

  1. customthe precipitate was removed by filtration
  2. washThe clear solution was washed with water
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum
  6. customThe residue was purified by Varia HPLC (10% acetonitrile/water)

Sources & evidence

ORD record
ord-0839b86277dd4bccb177a00036985fcc
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Linked notes

Loading…