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

HRID 1777551Notes

Reaction equation

HRID 1777551 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 for 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 thiosulfate, dried 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 the title compound 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 thiosulfate
  4. customdried
  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-9e6e4ccb5e6d4e4b8adb07db75ebc5e2
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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