Water → 2,6-Difluoro-4-iodoaniline

HRID 1034107Notes

Reaction equation

HRID 1034107 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[I:10]Cl.O>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([I:10])[CH:6]=[C:5]([F:9])[C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24640Iodine chlorideHCID 796472,6-Difluoroaniline

Product 1

HCID 2789432,6-Difluoro-4-iodoanilineYield 48.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

60 g of 2,6-difluoroaniline was dissolved in 180 ml of acetic acid. A solution containing 75 g of iodine chloride dissolved in 48 ml of acetic acid was added dropwise therein, and then agitated at 80° C. for 2 hours. The reaction solution was poured into water, and the resulting deposited crystals were filtrated and washed with water. The crystals were recrystallized with methanol, vacuum distilled (125° C./22 mmHg), and recrystallized again with methanol to obtain 57 g of 2,6-difluoro-4-iodoaniline.

Workup

  1. additionwas added dropwise
  2. filtrationwere filtrated
  3. washwashed with water
  4. customThe crystals were recrystallized with methanol, vacuum
  5. distillationdistilled (125° C./22 mmHg)
  6. customrecrystallized again with methanol

Sources & evidence

ORD record
ord-b331ad4c882f4d778c63bb09feba3361
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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