2-Isopropylaniline → 4-Iodo-2-(propan-2-yl)aniline

HRID 1593075Notes

Reaction equation

HRID 1593075 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[Cl-].[I-:17]>C(O)(=O)C.C(OCC)(=O)C>[I:17][C:8]1[CH:7]=[CH:6][C:5]([NH2:10])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=1

Participants

6

Reactant 3

HCID 125612-IsopropylanilineHCID 517045Sodium AcetateHCID 22282805Iodide monochloride

Product 1

HCID 126679384-Iodo-2-(propan-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-isopropyl-phenylamine (262 mg, 1.94 mmol) and sodium acetate (159 mg, 1.94 mmol) in 5 mL acetic acid, was added iodide monochloride (409 mg, 2.58 mmol) at room temperature. The mixture was stirred at room temperature for 20 minutes, then diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic layers were combined and concentrated in vacuo to give a crude residue, which was purified by column chromatography (silica 5-25% EtOAc/hexane) to give 4-iodo-2-isopropyl-phenylamine.

Workup

  1. washwashed with saturated sodium bicarbonate
  2. concentrationconcentrated in vacuo
  3. customto give a crude residue, which
  4. customwas purified by column chromatography (silica 5-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-418f422171b7461eaa9adc007a0f8c4b
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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