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

HRID 1016660Notes

Reaction equation

HRID 1016660 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 91.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 10.0 g (0.04 mol) of N-(3-bromopropyl)phthalimide in 240 mL of acetone was treated with 41.7 g (0.25 mol) of potassium iodide and stirred at room temperature for 4 days. The reaction mixture was filtered and the filtrate was diluted with 800 mL of ether and filtered again through celite. The filtrate was then concentrated at reduced pressure. The resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL) to yield 10.71 g (91.1%) of 2 as off-white needles.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was diluted with 800 mL of ether
  3. filtrationfiltered again through celite
  4. concentrationThe filtrate was then concentrated at reduced pressure
  5. customThe resulting yellow solid was recrystallized from 550 mL of hexane (filtered hot and boiled down to 300 mL)

Sources & evidence

ORD record
ord-7c3628dc11bf4c528d546e9fa8b85970
Source dataset
uspto-grants-2002_11
Patent number
US06476199B1

Reaction notes

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