1,3-Dibromopropane → 2-(3-Bromopropoxy)-1H-isoindole-1,3(2H)-dione

HRID 495875Notes

Reaction equation

HRID 495875 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[Br:13][CH2:14][CH2:15][CH2:16]Br.C(N(CC)CC)C>CN(C=O)C>[C:3]1(=[O:12])[N:2]([O:1][CH2:16][CH2:15][CH2:14][Br:13])[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]12

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 2655692-(3-Bromopropoxy)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
47.5 °C

Procedure

A mixture of N-hydroxyphthalimide (16.3 g, 100 mmol) and 1,3-dibromopropane (20.19 g, 100 mmol) in dry DMF (150 mL) and triethyl amine (15.33 mL, 110 mmol) is stirred at 20 to 75° C. for 1 to 10 hours. After filtration, the mixture is evaporated to dryness in vacuo. The residue is purified by silica gel flash column chromatography to give the title compound.

Workup

  1. filtrationAfter filtration
  2. customthe mixture is evaporated to dryness in vacuo
  3. customThe residue is purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-122357df30bc46709670550b386ea652
Source dataset
uspto-grants-2005_09
Patent number
US06942966B1

Reaction notes

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