N-bromobutanimide → 1,5-Dibromo-2,4-difluorobenzene

HRID 1983501Notes

Reaction equation

HRID 1983501 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[Br:10]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([Br:10])[C:5]([F:8])=[CH:4][C:3]=1[F:9]

Participants

4

Procedure

A total of 1.6 g of 1-bromo-2,4-difluorobenzene was suspended in 8.29 ml of sulfuric acid, and 1.62 g of N-bromosuccinimide was added under ice-cooling. After stirring at room temperature for 17 hours, the reaction mixture was poured onto ice-water and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (hexane), to give 2.18 g of the title compound as a pale yellow oil.

Workup

  1. temperaturecooling
  2. additionthe reaction mixture was poured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified
  8. customseparated by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-93b6c234cfa547198798979cdb5549ed
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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