1-Bromo-3-(bromomethyl)-5-chlorobenzene → 2-(3-Bromo-5-chlorobenzyl)isoindoline-1,3-dione

HRID 917541Notes

Reaction equation

HRID 917541 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9]Br)[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:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[CH2:9][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 223242641-Bromo-3-(bromomethyl)-5-chlorobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 589629502-(3-Bromo-5-chlorobenzyl)isoindoline-1,3-dioneYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Step G3. A mixture of 1-bromo-3-(bromomethyl)-5-chlorobenzene (6 g, ˜21 mmol) and potassium phthalimide (3.15 g, 17 mmol) in DMF (50 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-Bromo-5-chlorobenzyl)isoindoline-1,3-dione (5.1 g, 85%) was obtained as white solid. 1H NMR (DMSO-d6): δδ3.72 (s, 2H), 7.43 (s, 1H), 7.51 (s, 1H), 7.52 (s, 1H), 7.84, 7.86 (d, 2H), 8.05, 8.07 (d, 2H).

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-6b1bad60a5f840f3ac7055b20ffabba2
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

Loading…