N-bromobutanimide → 4-bromo-3-fluoro-2-nitroaniline

HRID 1429214Notes

Reaction equation

HRID 1429214 reaction equation
[F:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:12]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Br:12][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[F:1]

Participants

5

Reactant 2

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

Product 1

HCID 27831584-bromo-3-fluoro-2-nitroanilineYield 98.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-fluoro-2-nitroaniline (2.1 g, 13.4 mmol) in DMF (30 mL) at 0° C. was added a solution of N-bromosuccinimide (2.4 g, 13.4 mmol) in DMF (20 mL). The resulting solution was stirred at 0° C. for 30 minutes and then warmed to room temperature over 1 hour. The solution was diluted with EtOAc, washed with H2O and brine, dried over MgSO4, filtered and concentrated to give the title compound (3.1 g, 97%).

Workup

  1. temperaturewarmed to room temperature over 1 hour
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4c9166d5d8cd4044bc5009f204726334
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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