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

HRID 2040921Notes

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+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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

Conditions

Temperature: 120 °C

Procedure

An amount of 27.6 g (0.269 mol) of 2,2-difluoro-1-chloroethane, 2.16 g (6.73 mmol) of tetra(n-butyl)ammonium bromide and 20 g (0.135 mol) of phthalimide are dissolved in 95 g of N,N-dimethylformamide and treated with 46.96 g (0.336 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 150 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 28.5 g of 2-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dione with a purity of 97.4% is obtained. This corresponds to a yield of 97.7% of theory.

Workup

customAfter the end of the reaction
temperaturecooling
customis carried out to ambient temperature
customthe solvent is exhaustively removed under vacuum
additionThe remaining residue is treated with 150 ml of water
filtrationthe solid is filtered off
washThe filter residue is washed twice with water
customthe product is dried under vacuum

Sources & evidence

ORD record: ord-93240e026dcf4615aff1ef2b5f0ec7b9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580973B2

Reaction notes

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