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

HRID 2379116Notes

Reaction equation

HRID 2379116 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 (10g, 61.5mmol) in 1:1 acetic acid/methylene chloride (200mL). Add N-iodosuccinimide (16.9g, 61.5mmol) as a solid and stir at room temperature in the absence of light for 8 hours. Pour the solution into saturated sodium hydrogen carbonate (200mL) and extract into methylene chloride (100mL). Wash with saturated sodium hydrogen carbonate (200mL), dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound (8.1g, 45%); mp 61°-63° C.

Workup

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

Sources & evidence

ORD record
ord-cfbec2838c364f0aa53c5502b7dbe5a6
Source dataset
uspto-grants-1994_11
Patent number
US05360814

Reaction notes

Loading…