3,4-Dichloroaniline → 4,5-Dichloro-2-iodoaniline

HRID 925318Notes

Reaction equation

HRID 925318 reaction equation
[I:1]Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[Cl:11])[NH2:7]>C(O)(=O)C>[Cl:11][C:10]1[C:4]([Cl:3])=[CH:5][C:6]([NH2:7])=[C:8]([I:1])[CH:9]=1

Participants

4

Reactant 2

HCID 72573,4-DichloroanilineHCID 24640Iodine chloride

Product 1

HCID 109131874,5-Dichloro-2-iodoanilineYield 43.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine monochloride (1.39 mL; 27.77 mmol) was added to a solution of 3,4-dichloroaniline (4.50 g; 27.77 mmol) in acetic acid (15 mL) and the resulting mixture was stirred 30 minutes at room temperature. The solution was concentrated to dryness, neutralized with sodium bicarbonate and extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium thiosulphate, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 3.46 g (43%) of 4,5-dichloro-2-iodoaniline as a brown solid.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with a saturated solution of sodium thiosulphate
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-bc7c0da340e949d1b7c406bbc86c7886
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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