Water → HCID 22219483, compound

HRID 1793940Notes

Reaction equation

HRID 1793940 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:4][CH:3]=1.O.F[B-](F)(F)F.[O:23]=[N+:24]=[O:25]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:16])[C:12]([F:14])([F:15])[F:13])=[C:6]([N+:24]([O-:25])=[O:23])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1518036N-(4-Bromophenethyl)-2,2,2-trifluoroacetamideHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 22219483HCID 22219483, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 23.89 g of N-[2-(4-bromophenyl)ethyl]-2,2,2-trifluoroacetamide in 200 mL of acetonitrile was added in one portion 13.87 g of nitronium tetrafluoroborate under ice-cooling. After the mixture was stirred at room temperature for 15 minutes, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 11.03 g of N-[2-(4-bromo-2-nitrophenyl)ethyl]-2,2,2-trifluoroacetamide.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-45c48fdf23834d0da6cc5160227f3e88
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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