Potassium Iodide → 2-(4-Iodobutyl)-1H-isoindole-1,3(2H)-dione

HRID 1107999Notes

Reaction equation

HRID 1107999 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[I-:17].[K+]>CC(C)=O>[I:17][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16]

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 2302852-(4-Iodobutyl)-1H-isoindole-1,3(2H)-dioneYield 68.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5.0 g (0.018 mol) of N-(4-bromobutyl)phthalimide in 116 mL of acetone was treated with 20.7 g (0.125 mol) of potassium iodide and stirred at room temperature for 5 days. The reaction was filtered and the filtrate was diluted with 400 mL of ether, then filtered again through celite. The filtrate was concentrated at reduced pressure. The resulting solid was recrystallized from 300 mL of hexane (filtered hot and boiled down to 150 mL) to yield 4.0 g (68.6%) of 3 as white needles.

Workup

  1. filtrationThe reaction was filtered
  2. additionthe filtrate was diluted with 400 mL of ether
  3. filtrationfiltered again through celite
  4. concentrationThe filtrate was concentrated at reduced pressure
  5. customThe resulting solid was recrystallized from 300 mL of hexane (filtered hot and boiled down to 150 mL)

Sources & evidence

ORD record
ord-bf79eda00a9c4761836bb5b1e604f93e
Source dataset
uspto-grants-2000_05
Patent number
US06063908

Reaction notes

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