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

HRID 1956116Notes

Reaction equation

HRID 1956116 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

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-0f75ced06abc411fb95d92dd437e8398
Source dataset
uspto-grants-1998_07
Patent number
US05780241

Reaction notes

Loading…