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

HRID 711689

Reaction equation

HRID 711689 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-9801ae079fad4f028e95c62fb9d6110c
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Linked notes

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