Phthalimide → 2-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dione

HRID 2040925Notes

Reaction equation

HRID 2040925 reaction equation
[F:1][CH:2]([F:5])[CH2:3]Cl.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][CH:2]([F:5])[CH2:3][N:10]1[C:6](=[O:16])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:11]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 2736499Chlorodifluoroethane (mixed isomers)

Product 1

HCID 866684402-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dioneYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

An amount of 27.6 g (0.269 mol) of 2,2-difluoro-1-chloroethane and 20 g (0.135 mol) of phthalimide are dissolved in 95 g of N,N-dimethylformamide and treated with 56.3 g (0.403 mol) of potassium carbonate. The reaction mixture is stirred in an autoclave under pressure at 120° C. for 16 h. After the end of the reaction, cooling is carried out to ambient temperature and the solvent is exhaustively removed under vacuum. The remaining residue is treated with 100 ml of water and the solid is filtered off. The filter residue is washed twice with water and the product is dried under vacuum. An amount of 22.2 g of 2-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dione with a purity of 98.4% is obtained. This corresponds to a yield of 77% of theory.

Workup

  1. customAfter the end of the reaction
  2. temperaturecooling
  3. customis carried out to ambient temperature
  4. customthe solvent is exhaustively removed under vacuum
  5. additionThe remaining residue is treated with 100 ml of water
  6. filtrationthe solid is filtered off
  7. washThe filter residue is washed twice with water
  8. customthe product is dried under vacuum

Sources & evidence

ORD record
ord-9529fe7e9042445493775c56c8342820
Source dataset
uspto-grants-2013_11
Patent number
US08580973B2

Reaction notes

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