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

HRID 1107998Notes

Reaction equation

HRID 1107998 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-f9de55548adc4c2789749d6cfa186a97
Source dataset
uspto-grants-2000_05
Patent number
US06063908

Reaction notes

Loading…