Chlorosuccinimide → 4-Bromo-2-chloro-3,5-difluoroaniline

HRID 1270729

Reaction equation

HRID 1270729 reaction equation
[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:10].C1C(=O)N([Cl:18])C(=O)C1>CN(C=O)C.CCOCC>[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([Cl:18])[C:3]=1[F:10]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 27362604-Bromo-3,5-difluoroaniline

Product 1

HCID 184515214-Bromo-2-chloro-3,5-difluoroaniline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Bromo-3,5-difluoroaniline (10.5 g, 50.5 mmol) is dissolved in DMF (100 mL). NCS (28.6 g, 50.5 mmol) is added portionwise at room temperature. After 48 hours, the reaction is diluted with Et2O and washed with brine. The separated organic phase is dried (Na2SO4) and concentrated to give an oil. The residue is purified by column chromatography (EtOAc/hexanes) to give 4-bromo-2-chloro-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
  5. customThe residue is purified by column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-412f43e343fe4ce2a34aeef9f39f29dd
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Linked notes

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