HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2040922
Notes
Print preview

Reaction equation

HRID 2040922 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

HCID 866684402-(2,2-difluoroethyl)-1H-isoindole-1,3(2H)-dioneYield 87.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 6228
Dimethylformamide
Solvent

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

  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-cd3f187c5ce74299936653eb11566320
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08580973B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes