Potassium Carbonate → 4-Bromo-3-chloro-6-iodo-2-methylaniline

HRID 1909897Notes

Reaction equation

HRID 1909897 reaction equation
Cl.[Br:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[C:4]=1[Cl:11].C([O-])(=O)C.[Na+].[I:17]N1C(=O)CCC1=O.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.C(O)(=O)C>[Br:2][C:3]1[CH:9]=[C:8]([I:17])[C:6]([NH2:7])=[C:5]([CH3:10])[C:4]=1[Cl:11]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 120273N-IodosuccinimideHCID 517045Sodium AcetateHCID 866544344-Bromo-3-chloro-2-methylaniline hydrochloride

Product 1

HCID 583067804-Bromo-3-chloro-6-iodo-2-methylanilineYield 96.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-bromo-3-chloro-2-methyl aniline hydrochloride (1.0 g), sodium acetate (0.5 g), and acetic acid (15 mL) was added N-iodosuccinimide (1.0 g) under water-cooling. The reaction mixture was stirred at room temperature for 3.5 hours. To the reaction mixture were added ethyl acetate and water, and alkalified by adding potassium carbonate. Then, a liquid-separation operation was carried out, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10) to obtain 4-bromo-3-chloro-6-iodo-2-methylaniline (1.3 g).

Workup

  1. temperaturecooling
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-90:10)

Sources & evidence

ORD record
ord-5c7205a44212413690f5446e8c8d412c
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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