Potassium Iodide → 2-(3-Iodo-propyl)-isoindole-1,3-dione

HRID 230078Notes

Reaction equation

HRID 230078 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[I-:16].[K+]>CC(C)=O>[I:16][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15]

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 2302832-(3-Iodo-propyl)-isoindole-1,3-dioneYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 50.0 g (0.187 mol) of N-(3-bromopropyl)phthalimide in 1.2 L of acetone was treated with 208.5 g of potassium iodide and stirred at room temperature for 4 days. The reaction was filtered and the filtrate was diluted with 4 L of ether. This was then filtered through CELITE. The filtrate was concentrated under reduced pressure to a yellow solid. This was recrystallized from hexane to yield 46.5 g (79%) of off-white solid.

Workup

  1. filtrationThe reaction was filtered
  2. additionthe filtrate was diluted with 4 L of ether
  3. filtrationThis was then filtered through CELITE
  4. concentrationThe filtrate was concentrated under reduced pressure to a yellow solid
  5. customThis was recrystallized from hexane

Sources & evidence

ORD record
ord-5b7225ab5fa64d29b8cf65242ea8936a
Source dataset
uspto-grants-2009_07
Patent number
US07566549B2

Reaction notes

Loading…