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

HRID 375219

Reaction equation

HRID 375219 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[I:10]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)Cl>[I:10][C:3]1[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:4]=1[NH2:5]

Participants

5

Reactant 3

HCID 122813,5-DichloroanilineHCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 100169433,5-Dichloro-2-iodoanilineYield 45.7%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

Dissolve 3,5-dichloroaniline (10 g, 61.5 mmol) in 1:1 acetic acid/methylene chloride (200 mL). Add N-iodosuccinimide (16.9 g, 61.5 mmol) as a solid and stir at room temperature in the absence of light for 8 hours. Pour the solution into saturated sodium hydrogen carbonate (200 mL) and extract into methylene chloride (100 mL). Wash with saturated sodium hydrogen carbonate (200 mL), dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound (8.1 g, 45%); mp 61°-63° C.

Workup

  1. extractionextract into methylene chloride (100 mL)
  2. washWash with saturated sodium hydrogen carbonate (200 mL)
  3. dry with materialdry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-5a73e3d4f0ea4a83ac240edfe093d315
Source dataset
uspto-grants-1996_01
Patent number
US05484814

Linked notes

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