N-bromobutanimide → (2-Bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine

HRID 530917Notes

Reaction equation

HRID 530917 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].[Br:16]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C>[Br:16][C:8]1[CH:7]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([N+:13]([O-:15])=[O:14])[C:3]=1[NH:2][CH3:1]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 88405Benzenamine, N-methyl-2-nitro-4-(trifluoromethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 68878922(2-Bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of methyl-(2-nitro-4-trifluoromethyl-phenyl)-amine (16 g) and acetonitrile (200 ml) was added N-bromosuccinimide (15 g) while ice-cooling. The reaction mixture was stirred at room temperature for 5 hours. To the resulting reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and then the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give (2-bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine (15 g).

Workup

  1. temperaturecooling
  2. customTo the resulting reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa604e7528964622be210599bedf4e02
Source dataset
uspto-grants-2016_05
Patent number
US09353110B2

Reaction notes

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