N-bromobutanimide → 4-Bromo-3,5-difluoroaniline

HRID 1270728

Reaction equation

HRID 1270728 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].C1C(=O)N([Br:17])C(=O)C1>CN(C=O)C.CCOCC>[Br:17][C:8]1[C:2]([F:1])=[CH:3][C:4]([NH2:5])=[CH:6][C:7]=1[F:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 965953,5-Difluoroaniline

Product 1

HCID 27362604-Bromo-3,5-difluoroaniline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3,5-Difluoroaniline (10.0 g, 77.5 mmol) is dissolved in DMF (100 mL). NBS (13.9 g, 78.0 mmol) is added portionwise at room temperature. After stirring overnight at room temperature, the reaction mixture is diluted with Et2O and washed with brine. The separated organic phase is dried (Na2SO4) and concentrated to give an oil which is purified by column chromatography (methylene chloride/hexanes) to give 4-bromo-3,5-difluoroaniline.

Workup

  1. washwashed with brine
  2. dry with materialThe separated organic phase is dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give an oil which
  5. customis purified by column chromatography (methylene chloride/hexanes)

Sources & evidence

ORD record
ord-e552a0d6f13146c99cc37f51be6c777b
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Linked notes

Loading…