Dimethylformamide → 2-[3-(4-Fluoro-2-nitrophenoxy)propyl]isoindole-1,3-dione

HRID 238311

Reaction equation

HRID 238311 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].CN(C)C=O.[F:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([N+:35]([O-:37])=[O:36])[CH:29]=1>O>[F:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:8][CH2:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]2=[O:21])=[C:30]([N+:35]([O-:37])=[O:36])[CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 1362364-Fluoro-2-nitrophenol

Product 1

HCID 669171582-[3-(4-Fluoro-2-nitrophenoxy)propyl]isoindole-1,3-dioneYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (10.8 g, 78.1 mmol) and N-(3-bromopropyl)phthalimide (12.1 g, 45.1 mmol) were added to a N,N-dimethylformamide (DMF) solution (80 ml) of 4-fluoro-2-nitrophenol (6.0 g, 38.2 mmol), and the mixture was stirred at 60° C. for 4 hours. After the reaction mixture was cooled to room temperature, water (200 ml) was added, and the reaction mixture was then cooled with ice. The precipitated insoluble matter was collected by filtration. After being washed with water (50 ml×3), the substance remaining in the filter was air-dried, giving 13.2 g of powdery pale yellow 2-[3-(4-fluoro-2-nitrophenoxy)propyl]isoindole-1,3-dione (yield: 100%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. temperaturethe reaction mixture was then cooled with ice
  3. filtrationThe precipitated insoluble matter was collected by filtration
  4. washAfter being washed with water (50 ml×3)
  5. customwas air-dried

Sources & evidence

ORD record
ord-eac80c56130c4a7aa034e5f0c148058a
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Linked notes

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