Bromine → 4-Bromo-2,5-difluoroaniline

HRID 1607178Notes

Reaction equation

HRID 1607178 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[Br:10]Br>CC(O)=O>[Br:10][C:7]1[C:6]([F:9])=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 677752,5-Difluoroaniline

Product 1

HCID 27732854-Bromo-2,5-difluoroanilineYield 97.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 100 g of 2,5-difluoroaniline and 1150 mL of AcOH is added over 1.3 hours a solution of 40.2 mL of Br2 in 350 mL of AcOH at a temperature of 15°-20°. The pink suspension is stirred 30 minutes longer and then evaporated in vacuo. The residue is basified with 50% NaOH (ice is added to keep the temperature below 35°). Extraction of the free base with 1 L of CH2Cl2 and washing of the extract with 2×100 mL of H2O, drying with Na2SO4 and evaporation in vacuo gives 157 g (97.5% yield) of 4-bromo-2,5-difluoroaniline, m.p. 73°-75°. The mass spectrum had a M+1 ions at 208,210.

Workup

  1. customevaporated in vacuo
  2. additionis added
  3. customthe temperature below 35°
  4. extractionExtraction of the free base with 1 L of CH2Cl2
  5. washwashing of the
  6. extractionextract with 2×100 mL of H2O
  7. dry with materialdrying with Na2SO4 and evaporation in vacuo

Sources & evidence

ORD record
ord-abd31413eb7e4e649bf64f7c5dc8381e
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

Loading…