Iodine → Aniline, 2,6-dichloro-4-iodo-

HRID 1270712Notes

Reaction equation

HRID 1270712 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].C(=O)(O)[O-].[Na+].[I:15]I>>[Cl:1][C:2]1[CH:8]=[C:7]([I:15])[CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4]

Participants

4

Reactant 3

HCID 807IodineHCID 118462,6-DichloroanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 12770Aniline, 2,6-dichloro-4-iodo-

Conditions

Temperature
60 °C

Procedure

2,6-Dichloroaniline (16.2 g, 0.1 mol) is suspended in a solution of sodium bicarbonate (8.6 g, 0.1 mol in 100 mL of water) and warmed to 60° C. Elemental iodine (25.4 g, 0.1 mol) is added portionwise and the resulting mixture stirred at 60° C. for 3 days. After cooling to room temperature, the reaction mixture is partitioned between CH2Cl2 (250 mL) and saturated sodium bisulfite solution (500 mL). The aqueous layer is re-extracted with additional CH2Cl2 (250 mL) and the combined organic layers dried (MgSO4) and concentrated by rotary evaporator. The residual oil is purified by flash chromatography (9:1 hexanes/EtOAc) to give 2,6-dichloro-4-iodoaniline (m.p. 100–102° C.).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture is partitioned between CH2Cl2 (250 mL) and saturated sodium bisulfite solution (500 mL)
  3. extractionThe aqueous layer is re-extracted with additional CH2Cl2 (250 mL)
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe residual oil is purified by flash chromatography (9:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-f13304d88833498182617bbccea22fb7
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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