Bromine → 2-Bromo-3-chloro-4-fluoro-6-nitroaniline

HRID 1761643Notes

Reaction equation

HRID 1761643 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:6]([N+:10]([O-:12])=[O:11])=[CH:7][C:8]=1[F:9])[NH2:5].[Br:13]Br>C(O)(=O)C>[Br:13][C:3]1[C:2]([Cl:1])=[C:8]([F:9])[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:4]=1[NH2:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 5178355-Chloro-4-fluoro-2-nitroaniline

Product 1

HCID 137487952-Bromo-3-chloro-4-fluoro-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a solution of 3-chloro-4-fluoro-6-nitroaniline (200.3 g) in acetic acid (1.5 litter) was added bromine (339 g) during a period of 80 minutes at 50° C. under stirring and stirred for further 2 hours. The reaction mixture was poured into ice water (3 litter) and the resulting precipitate was collected by filtration, washed with water and added to a mixture of concentrated hydrochloric acid (300 ml) and ethanol (1.2 litter). The mixture was refluxed for 8.5 hrs. After cooling, the precipitate was collected by filtration and washed with water and dried. The title compound thus obtained weighed 235.6 g as yellow needles, mp 146°-147° C.

Workup

  1. stirringstirred for further 2 hours
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. additionadded to a mixture of concentrated hydrochloric acid (300 ml) and ethanol (1.2 litter)
  5. temperatureThe mixture was refluxed for 8.5 hrs
  6. temperatureAfter cooling
  7. filtrationthe precipitate was collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-323cb1c41539483a969603e97957f6ad
Source dataset
uspto-grants-1989_05
Patent number
US04826982

Reaction notes

Loading…