3,5-Dibromobenzyl bromide → 2-(3,5-Dibromobenzyl)isoindoline-1,3-dione

HRID 917544Notes

Reaction equation

HRID 917544 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[C:4]([Br:10])[CH:3]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Br:10])[CH:3]=1)[CH2:8][N:15]1[C:11](=[O:21])[C:12]2[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14]1=[O:16]

Participants

4

Reactant 2

HCID 1434273,5-Dibromobenzyl bromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 589629162-(3,5-Dibromobenzyl)isoindoline-1,3-dioneYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1,3-dibromo-5-(bromomethyl)benzene (1.1 g, ˜3.3 mmol) and potassium phthalimide (0.62 g, 3.3 mmol) in DMF (10 ml) was heated at 120° C. for 2 hours. After cooled down, a white solid precipitated. The solid was filtered and washed with ethanol, then dried in vacuum. 2-(3,5-dibromobenzyl)isoindoline-1,3-dione (1.1 g, 83%) was obtained as white solid.

Workup

  1. temperatureAfter cooled down
  2. customa white solid precipitated
  3. filtrationThe solid was filtered
  4. washwashed with ethanol
  5. customdried in vacuum

Sources & evidence

ORD record
ord-6e9cde365f1144f59c5e14c9be0faa94
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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