2-Ethylaniline → 2-ethyl-4-iodoaniline

HRID 230855Notes

Reaction equation

HRID 230855 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-dc5662bb5c8447e4bd184b0514626ac2
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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