Bromine → 4-Bromo-2,6-difluoroaniline

HRID 1741549Notes

Reaction equation

HRID 1741549 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:5]=1[NH2:6].S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[Br:1][C:9]1[CH:10]=[C:4]([F:3])[C:5]([NH2:6])=[C:7]([F:11])[CH:8]=1

Participants

7

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 796472,6-DifluoroanilineHCID 517045Sodium Acetate

Product 1

HCID 6101914-Bromo-2,6-difluoroanilineYield 81.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of bromine (127.0 g, 0.79 mol) in glacial acetic acid (200 ml) was added slowly, dropwise to a stirred solution of 2,6-difluoroaniline (101.5 g, 0.79 mol) in glacial acetic acid (550 ml) keeping the temperature below 25° C. The mixture was stirred at room temperature for 2 h, and then sodium thiosulphate (50 g), sodium acetate (125 g) and water (700 ml) were added and the mixture was cooled in a refrigerator overnight. The product was filtered off, dissolved in ether, and the ether phase was washed with water, 10% sodium hydroxide, water and dried (MgSO4). The solvent was removed in vacuo to yield a pale yellow solid (134 g) which was steam distilled to give a colourless solid.

Workup

  1. customthe temperature below 25° C
  2. temperaturethe mixture was cooled in a refrigerator overnight
  3. filtrationThe product was filtered off
  4. dissolutiondissolved in ether
  5. washthe ether phase was washed with water, 10% sodium hydroxide, water
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a0d4f36e584e429fbf5c143f07a37c50
Source dataset
uspto-grants-1994_08
Patent number
US05334327

Reaction notes

Loading…