Dichloromethane → (4-Iodo-2,5-Dimethylphenyl)Amine

HRID 2113279Notes

Reaction equation

HRID 2113279 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].ClCCl.C(=O)(O)[O-].[Na+].C[N+](C)(C)C.Cl[I-:24]Cl>O.CO>[I:24][C:7]1[C:6]([CH3:9])=[CH:5][C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 72592,5-DimethylanilineHCID 516892Sodium BicarbonateHCID 11737348Tetramethylammonium Dichloroiodate

Product 1

HCID 4770984(4-Iodo-2,5-Dimethylphenyl)AmineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,5-dimethylaniline (20 g, 165 mmol) in a 1:1 mixture of dichloromethane and methanol (400 mL) was added sodium bicarbonate (20.8 g, 250 mmol) and tetramethylammonium dichloroiodate(I) (44.7 g, 165 mmol). The resulting mixture was stirred at room temperature for 1 hour and then water was added (500 mL). The organic layer was removed and washed with 5% aqueous sodium thiosulfate (500 mL) and brine (500 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide 4-iodo-2,5-dimethylphenylamine (39.6 g, 98% yield). The product was used without further purification.

Workup

  1. customThe organic layer was removed
  2. washwashed with 5% aqueous sodium thiosulfate (500 mL) and brine (500 mL)
  3. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5d6a335d76804c6eb443e77aeafa1430
Source dataset
uspto-grants-2009_04
Patent number
US07524965B2

Reaction notes

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