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

HRID 392019Notes

Reaction equation

HRID 392019 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-380ad7b8011a4f919fa0550ef8039029
Source dataset
uspto-grants-2004_10
Patent number
US06800444B1

Reaction notes

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