Bromine → 4-Bromo-2,6-difluoroaniline

HRID 1503824Notes

Reaction equation

HRID 1503824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH2:9].[Br:10]Br>C(O)(=O)C>[Br:10][C:6]1[CH:7]=[C:2]([F:1])[C:3]([NH2:9])=[C:4]([F:8])[CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 796472,6-Difluoroaniline

Product 1

HCID 6101914-Bromo-2,6-difluoroaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,6-Difluorobenzeneamine (6.0 g, 45 mmol) was dissolved in acetic acid (20 mL) and bromine (2.4 mL, 50 mmol) was added and the mixture was stirred at ambient temperature for 15 minutes. After concentration, the residue was treated with aqueous sodium carbonate and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 25/1 petroleum ether/ethyl acetate to give the title compound. MS: 208 (M+H+).

Workup

  1. concentrationAfter concentration
  2. additionthe residue was treated with aqueous sodium carbonate
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (200-300 mesh)
  9. washeluting with 25/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-9947f83dcc7740cba1c53f5289003446
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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