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

HRID 1078427Notes

Reaction equation

HRID 1078427 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-f451619b860f4184a339dd18c136f915
Source dataset
uspto-grants-1996_08
Patent number
US05547991

Reaction notes

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