Pyrimidine → 4-Bromo-2,6-difluoroaniline

HRID 1589752Notes

Reaction equation

HRID 1589752 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].N1C=CC=NC=1>C(Cl)(Cl)Cl>[Br:1][C:9]1[CH:10]=[C:4]([F:3])[C:5]([NH2:6])=[C:7]([F:11])[CH:8]=1

Participants

5

Reactant 3

HCID 9260PyrimidineHCID 24408BromineHCID 796472,6-Difluoroaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

328 g (2.05 mol) of bromine was dissolved in 390 cm3 of chloroform and added drop-wise, while stirring, to a solution of 252 g (1.95 mol) of 2,6-difluoroaniline and 170 g (2.15 mol) of anhydrous pyrimidine dissolved in 780 cm3 of chloroform, over 2 hours. The solution was stirred at room temperature for 2 hours and washed with water. The chloroform was distilled off and the residue was distilled under reduced pressure (110° C./30 mmHg). The crystals formed were recrystallized from hexane to yield 340 g (1.63 mol) of 4-bromo-2,6-difluoroaniline.

Workup

  1. additionadded drop-wise
  2. washwashed with water
  3. distillationThe chloroform was distilled off
  4. distillationthe residue was distilled under reduced pressure (110° C./30 mmHg)
  5. customThe crystals formed
  6. customwere recrystallized from hexane

Sources & evidence

ORD record
ord-48b71e699a394592a61bc89ddd897b83
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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