4-Nitrobenzyl bromide → 2-(4-Nitro-benzyl)-isoindole-1,3-dione

HRID 1428774Notes

Reaction equation

HRID 1428774 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K].CN(C)C=O>>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 660114-Nitrobenzyl bromideHCID 86680223HCID 86680223, compound

Product 1

HCID 2708672-(4-Nitro-benzyl)-isoindole-1,3-dioneYield 120.9%

Procedure

To a solution of 1-(bromomethyl)-4-nitrobenzene (1.1 g, 4.69 mmol) in dimethylformamide potassium phthalimide (1.9 g, 10.314 mmol) was added. The mixture was reacted for overnight, extracted with ethyl acetate and washed with brine (3×20 mL). Drying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography gave 2-(4-nitrobenzyl)isoindoline-1,3-dione (1.6 g, 99%).

Workup

  1. customThe mixture was reacted for overnight
  2. extractionextracted with ethyl acetate
  3. washwashed with brine (3×20 mL)
  4. dry with materialDrying over magnesium sulfate, evaporation of the ethyl acetate and purification by column chromatography

Sources & evidence

ORD record
ord-fe64d92478eb4c289ecee2e04e9b8f93
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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