N-bromobutanimide → 4-Bromo-5-fluoro-2-nitroaniline

HRID 475209Notes

Reaction equation

HRID 475209 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].C1C(=O)N([Br:19])C(=O)C1>CC(O)=O>[Br:19][C:3]1[C:2]([F:1])=[CH:8][C:6]([NH2:7])=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 753995-Fluoro-2-nitroaniline

Product 1

HCID 219119284-Bromo-5-fluoro-2-nitroanilineYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-fluoro-2-nitroaniline (1.5 g, 9.61 mmol) and NBS (1.7 g, 9.55 mmol) in HOAc (75 mL) was heated at reflux for 90 min. The reaction mixture was then poured into ice water (300 mL) and stirred for 10 min. A bright yellow precipitate was collected by filtration and dried in vacuo overnight to afford 1.57 g (76%) of 4-bromo-5-fluoro-2-nitroaniline (96): MS (ESI) m/z=235 [M+1]+.

Workup

  1. temperatureat reflux for 90 min
  2. filtrationA bright yellow precipitate was collected by filtration
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-a020769fe92f4399a52952fabeb6158e
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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