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Phthalimide potassium salt → HCID 71255158, compound

HRID 539978
Notes
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Reaction equation

HRID 539978 reaction equation
Br[CH2:2][CH:3]([F:7])[CH2:4][CH2:5]Br.[C:8]1(=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[NH:9]1.[K]>CN(C)C=O.C(OCC)(=O)C>[F:7][CH:3]([CH2:4][CH2:5][N:9]1[C:10](=[O:17])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]1=[O:18])[CH2:2][N:9]1[C:10](=[O:17])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]1=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 574712831,4-Dibromo-2-fluorobutane

Product 1

HCID 71255158HCID 71255158, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1,4-dibromo-2-fluoro-butane (4.0 g, 17.09 mmol) in N,N-dimethylformamide (60 mL) was added potassium 2,3-dihydro-1H-isoindole-1,3-dione (9.5 g, 51.27 mmol). The reaction mixture was stirred at 100° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate (60 mL), washed with water (60 mL), brine (60 mL), dried over sodium sulfate, and concentrated in vacuo to afford 4.5 g of 2,2′-(2-fluorobutane-1,4-diyl)bis(1H-isoindole-1,3(2H)-dione) as a white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water (60 mL), brine (60 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e42bf9376638492aac3d55f56f1d2fa8
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871756B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes