Potassium Iodide → 4-Bromo-N-methylphthalimide

HRID 1874074Notes

Reaction equation

HRID 1874074 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2C(NC(=O)[C:3]=12)=O.[C:13](=[O:16])([O-])[O-].[K+].[K+].[I-].[K+].CI.[CH3:23][N:24]([CH:26]=[O:27])C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10](=[CH:11][CH:12]=1)[C:26](=[O:27])[N:24]([CH3:23])[C:13]2=[O:16]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 226073074-Bromo-1H-isoindole-1,3(2H)-dione

Product 1

HCID 7901054-Bromo-N-methylphthalimide

Conditions

Temperature
0 °C

Procedure

A mixture of 3-bromophthalimide (10.0 g, 44.2 mmol), potassium carbonate (12.2 g, 88.5 mmol) and potassium iodide (50 mg, 0.30 mmol) are stirred in 80 mL DMF for 15 min. The reaction mixture is cooled to 0° C., methyl iodide (3.04 mL, 48.7 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is filtered, the solids are washed with DMF and the filtrate is poured in water. The mixture is extracted with ethyl acetate and the combined organic phases are washed several times with water, dried over MgSO4 and concentrated in vacuo. Yield: 7.10 g.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe solids are washed with DMF
  3. additionthe filtrate is poured in water
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe combined organic phases are washed several times with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4697867f0e844816a44d6cd6cad41b1a
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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