Water → 2-(3-Fluoropropyl)-1H-isoindole-1,3(2H)-dione

HRID 1247490Notes

Reaction equation

HRID 1247490 reaction equation
[F:1][CH2:2][CH2:3][CH2:4]OS(C)(=O)=O.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.[K].O>CN(C=O)C>[F:1][CH2:2][CH2:3][CH2:4][N:14]1[C:10](=[O:20])[C:11]2[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:13]1=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 2483883-Fluoropropyl methanesulfonateHCID 24194345Phthalimide potassium salt

Product 1

HCID 219074482-(3-Fluoropropyl)-1H-isoindole-1,3(2H)-dioneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methanesulfonic acid 3-fluoro-propyl ester (34.5 g, 221 mmol) in 250 mL of anhydrous DMF was treated with solid potassium phthalimide (49 g, 265 mmol, 1.2 equiv) at 25° C. The resulting suspension was warmed to 70–80° C. for 2 hours. When 1H NMR showed that the reaction was complete, the reaction mixture was treated with H2O (200 mL). The aqueous solution was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (3×100 mL) and dried over MgSO4. The solvent was removed in vacuo to afford the desired 2-(3-fluoro-propyl)-isoindole-1,3-dione (45.4 g, 45.5 g theoretical, 99.7% yield) as a white powder.

Workup

  1. temperatureThe resulting suspension was warmed to 70–80° C. for 2 hours
  2. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with H2O (3×100 mL)
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e95c91e3a59d488ca3f64e9c820a2ea4
Source dataset
uspto-grants-2006_10
Patent number
US07129259B2

Reaction notes

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