Water → 4-bromo-3-fluoro-2-nitroaniline

HRID 475225Notes

Reaction equation

HRID 475225 reaction equation
[F:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:19])C(=O)C1.O>CN(C=O)C>[Br:19][C:7]1[CH:6]=[CH:5][C:4]([NH2:8])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[F:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 27828343-Fluoro-2-nitroaniline

Product 1

HCID 27831584-bromo-3-fluoro-2-nitroanilineYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 138 (25 g, 0.160 mol) in DMF (250 mL) at 0° C. was added dropwise a solution of NBS (28.5 g, 0.160 mol) in DMF (100 mL). The resulting mixture was stirred at 0° C. for 1 h and then at RT for another hour. After the completion of the reaction, the mixture was poured into water (4 L) and extracted with EtOAc. The combined organic layers were washed with water and brine solution, dried (Na2SO4), filtered and concentrated in vacuo to afford 34 g (90%) of 4-bromo-3-fluoro-2-nitro-phenylamine (140) as a yellow solid which was used without further purification.

Workup

  1. waitat RT for another hour
  2. customAfter the completion of the reaction
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine solution
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1afc592045e4de7a4afec0886b7cbb3
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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