2,4-Difluoroaniline → 2-Bromo-4,6-Difluoroaniline

HRID 1995455Notes

Reaction equation

HRID 1995455 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=1[NH2:6].C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[Br:1][C:7]1[CH:8]=[C:9]([F:11])[CH:10]=[C:4]([F:3])[C:5]=1[NH2:6]

Participants

6

Reactant 3

HCID 97092,4-DifluoroanilineHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 1362852-Bromo-4,6-Difluoroaniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of bromine (16.0 g; 0.10 mol) in glacial acetic acid (25 ml) is added dropwise to a solution of 2,4-difluoroaniline (12.9 g; 0.10 mol) in glacial acetic acid (75 ml) while maintaining the temperature of the reaction mixture below 25° C. The reaction mixture is stirred an additional 0.5 hour during which time a solution of sodium acetate (5.48 g; 0.137 mol) in water (100 ml) is added. The reaction mixture is then diluted with water (300 ml), the precipitated purple solid is filtered, washed with water (100 ml) and dried under vacuum.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture below 25° C
  2. additionis added
  3. filtrationthe precipitated purple solid is filtered
  4. washwashed with water (100 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ab8eab5a66b947449e43da3f90d75a14
Source dataset
uspto-grants-1983_09
Patent number
US04404402

Reaction notes

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