Acetonitrile → 1-[2-Amino-5-bromo-4-(trifluoromethyl)phenyl]ethanone

HRID 69114Notes

Reaction equation

HRID 69114 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].C(#N)C.[Br:18]N1C(=O)CCC1=O>C(OCC)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[C:5]([Br:18])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 468355001-(2-Amino-4-(trifluoromethyl)phenyl)ethan-1-one

Product 1

HCID 666961351-[2-Amino-5-bromo-4-(trifluoromethyl)phenyl]ethanoneYield 64.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 11.6 g of 1-[2-amino-4-(trifluoromethyl)phenyl]ethanone, 60 mL of acetonitrile, and 230 mL of diethyl ether was added 2.85 g of Amberlyst (registered trademark) 15, and 10.1 g of N-bromosuccinimide was added thereto in three times in an ice bath. After stirring for 30 minutes in an ice bath, the mixture was stirred at room temperature overnight. The insoluble material was filtered and washed with ethyl acetate. To the filtrate were added water and ethyl acetate, and the aqueous layer was separated. The organic layer was washed with a 10% aqueous sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate, and then solvent was evaporated. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 10.36 g of 1[2-amino-5-bromo-4-(trifluoromethyl)phenyl]ethanone.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature overnight
  3. filtrationThe insoluble material was filtered
  4. washwashed with ethyl acetate
  5. additionTo the filtrate were added water and ethyl acetate
  6. customthe aqueous layer was separated
  7. washThe organic layer was washed with a 10% aqueous sodium thiosulfate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customsolvent was evaporated
  10. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-195fbe543fdd481195764ad9f4a660d0
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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