Iodine → 5-Chloro-2-iodo-4-methylaniline

HRID 925313Notes

Reaction equation

HRID 925313 reaction equation
[I:1]I.[I-].[K+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[CH3:13])[NH2:9].C(=O)(O)[O-].[Na+]>O>[Cl:5][C:6]1[C:12]([CH3:13])=[CH:11][C:10]([I:1])=[C:8]([CH:7]=1)[NH2:9]

Participants

6

Reactant 4

HCID 807IodineHCID 4875Potassium IodideHCID 72553-Chloro-4-methylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 584754055-Chloro-2-iodo-4-methylanilineYield 24.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of iodine (9.86 g; 38.84 mmol) and potassium iodide (6.45 g; 38.84 mmol) in water was added dropwise to a suspension of 3-chloro-4-methylaniline (5.00 g; 35.31 g) in a solution of sodium bicarbonate (4.75 g; 56.50 mmol). The resulting mixture was stirred 72 hours at room temperature filtrated and the solid dissolved in dichloromethane, washed with a saturated solution of sodium thiosulphate, dried over magnesium sulphate and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to yield 2.30 g (24%) of 5-chloro-2-iodo-4-methylaniline as a brown solid.

Workup

  1. filtrationfiltrated
  2. dissolutionthe solid dissolved in dichloromethane
  3. washwashed with a saturated solution of sodium thiosulphate
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-be854a20e4d44e4d96e7b0c11403a1c8
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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