2-Ethylaniline → 2-ethyl-4-iodoaniline

HRID 2101677Notes

Reaction equation

HRID 2101677 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].C([O-])(=O)C.[Na+].[I:15]Cl>C(O)(=O)C>[CH2:1]([C:3]1[CH:9]=[C:8]([I:15])[CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2]

Participants

5

Reactant 3

HCID 113572-EthylanilineHCID 24640Iodine chlorideHCID 517045Sodium Acetate

Product 1

HCID 9540042-ethyl-4-iodoaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 2-ethylaniline (1.88 g, available from Aldrich) and sodium acetate (1.27 g) in acetic acid (20 ml) was added iodine monochloride (1 ml, available from Aldrich). The mixture was stirred at 20° C. for 90 min and then the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (25 ml) and saturated aqueous sodium carbonate solution (25 ml). The organic layer was dried using a hydrophobic frit and the solvent was removed in vacuo. Purification by C18 SPE eluting with 20% acetonitrile in water gave the title compound as a purple solid (0.402 g).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (25 ml) and saturated aqueous sodium carbonate solution (25 ml)
  3. customThe organic layer was dried
  4. customthe solvent was removed in vacuo
  5. customPurification by C18 SPE
  6. washeluting with 20% acetonitrile in water

Sources & evidence

ORD record
ord-8ac563d8d9264669af1e4c987121fa5b
Source dataset
uspto-grants-2009_08
Patent number
US07572915B2

Reaction notes

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