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

HRID 2040922Notes

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-chlorethane, 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 28.18 g (0.201 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 24.9 g of 2-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dione with a purity of 99.5% is obtained. This corresponds to a yield of 87.2% 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 100 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-cd3f187c5ce74299936653eb11566320
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580973B2

Reaction notes

Loading…