Chlorine → 2-Chloro-3,4-difluoro-6-nitroaniline

HRID 414373Notes

Reaction equation

HRID 414373 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Cl:13]Cl>C(O)(=O)C>[Cl:13][C:7]1[C:8]([F:9])=[C:2]([F:1])[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:6]

Participants

4

Reactant 2

HCID 24526ChlorineHCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 143652482-Chloro-3,4-difluoro-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a solution of 4,5-difluoro-2-nitroaniline (20 g) in acetic acid (200 ml) was boubled chlorine gas at 13° to 15° C. during 45 minutes. The reaction mixture was poured into ice water (500 ml) and extracted with dichloromethane. The organic layer was washed with 6% aqueous sodium carbonate and with water successively, dried over anhydrous sodium sulfate and then concentrated. The residue was purified with silica gel chromatography eluting with dichloromethane-n-hexane (1:4) and further recrystallized from hexane to give the title compound (2.91 g) as yellow needles, mp 86°-88° C.

Workup

  1. customat 13° to 15° C.
  2. customduring 45 minutes
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with 6% aqueous sodium carbonate and with water successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel chromatography
  8. washeluting with dichloromethane-n-hexane (1:4)
  9. customfurther recrystallized from hexane

Sources & evidence

ORD record
ord-5ab11999e3d74a1da3f66efd7cda325a
Source dataset
uspto-grants-1988_12
Patent number
US04791225

Reaction notes

Loading…