4-Bromo-1-(bromomethyl)-2-(methanesulfonyl)benzene → 2-(4-Bromo-2-methanesulfonylbenzyl)isoindole-1,3-dione

HRID 840653Notes

Reaction equation

HRID 840653 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:18]2[C:14](=[O:24])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17]2=[O:19])=[C:4]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:3]=1

Participants

5

Reactant 2

HCID 27610744-Bromo-1-(bromomethyl)-2-(methanesulfonyl)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 226200152-(4-Bromo-2-methanesulfonylbenzyl)isoindole-1,3-dioneYield 49.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.0 g of 4-bromo-1-bromomethyl-2-methanesulfonylbenzene and 2.0 g of potassium phthalimide are stirred at 100° C. for 1 h in 30 ml of anhydrous DMF. The mixture is allowed to cool, diluted with 200 ml of water and the suspension is stirred at RT for 30 minutes. The product is then filtered off and 1.8 g of a colorless solid are obtained, mp 188-190° C.

Workup

  1. temperatureto cool
  2. filtrationThe product is then filtered off

Sources & evidence

ORD record
ord-efa94f2feff94153ab12111dba6eb922
Source dataset
uspto-grants-2002_04
Patent number
US06369069B1

Reaction notes

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