Pyridine → 4-Bromo-2,6-difluoroaniline

HRID 1707520Notes

Reaction equation

HRID 1707520 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].N1C=CC=CC=1.[Br:16]Br>C(Cl)(Cl)Cl>[Br:16][C:7]1[CH:8]=[C:2]([F:1])[C:3]([NH2:4])=[C:5]([F:9])[CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 796472,6-Difluoroaniline

Product 1

HCID 6101914-Bromo-2,6-difluoroanilineYield 83.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

252 g (1.95 mol) of 2,6-difluoroaniline and 170 g (2.15 mol) of anhydrous pyridine were dissolved in 780 cm3 of chloroform, and a solution of 328 g (2.05 mol) of bromine dissolved in 390 cm3 of chloroform was added dropwise for 2 hours on an ice water bath while stirring, after which it was stirred for 2 hours at room temperature. After washing the reaction solution with water, the chloroform was removed, the residue was distilled under reduced pressure (b. p. 100° C./30 mmHg), and the crystals obtained were recrystallized from hexane to obtain 340 g (1.63 mol) of 4-bromo-2,6-difluoroaniline.

Workup

  1. additionwas added dropwise for 2 hours on an ice water bath
  2. stirringafter which it was stirred for 2 hours at room temperature
  3. washAfter washing the reaction solution with water
  4. customthe chloroform was removed
  5. distillationthe residue was distilled under reduced pressure (b. p. 100° C./30 mmHg)
  6. customthe crystals obtained
  7. customwere recrystallized from hexane

Sources & evidence

ORD record
ord-3e3fe58a197a4c71801d4e1be1a5b287
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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