Urea → 5-Fluoroisoindoline-1,3-dione

HRID 1966770Notes

Reaction equation

HRID 1966770 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=O)[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1.[NH2:13]C(N)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:7])[NH:13][C:9]2=[O:8]

Participants

4

Reactant 2

HCID 1176UreaHCID 675721,3-Isobenzofurandione, 5-fluoro-

Product 1

HCID 108990385-Fluoroisoindoline-1,3-dioneYield 100.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 4-fluorophthalic anhydride (5.0 g, 30.10 mmol) in toluene (15 mL) is added urea (2.1 g). The reaction mixture is stirred at refluxed for 16 h. The reaction mixture is allowed to cool to room temperature, concentrated under reduced pressure and triturated with H2O (250 mL) to afford 5-fluoro-isoindole-1,3-dione (5.0 g, 100%) as a white solid.

Workup

  1. temperatureat refluxed for 16 h
  2. concentrationconcentrated under reduced pressure
  3. customtriturated with H2O (250 mL)

Sources & evidence

ORD record
ord-4fbb8245889046fba2c7849229bb340b
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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