1-(Bromomethyl)-2-fluoro-4-nitrobenzene → 2-(2-Fluoro-4-nitrobenzyl)isoindoline-1,3-dione

HRID 1428736Notes

Reaction equation

HRID 1428736 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[F:12].[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C)C=O.C(OCC)(=O)C>[F:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:2][N:17]1[C:13](=[O:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16]1=[O:18]

Participants

5

Reactant 2

HCID 218861321-(Bromomethyl)-2-fluoro-4-nitrobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 708476692-(2-Fluoro-4-nitrobenzyl)isoindoline-1,3-dioneYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of crude 1-(bromomethyl)-2-fluoro-4-nitrobenzene (1.335 g, 5.705 mmol) in dimethylformamide was added potassium phthalimide (2.324 g, 12.55 mmol). The reaction mixture was stirred for 18 h The mixture was dissolved in ethyl acetate, washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography to give 2-(2-fluoro-4-nitrobenzyl)isoindoline-1,3-dione (1.229 g, 88%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-fc4dcd3c76ff4683b1b480eb91b28c6d
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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