Potassium Fluoride → HCID 57753244, compound

HRID 1930893Notes

Reaction equation

HRID 1930893 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:17]=[C:18]([F:20])[F:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-:21].[K+]>CS(C)=O.O.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 57753432HCID 57753432, compound

Product 1

HCID 57753244HCID 57753244, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 0.71 mmol 5-(2,2-difluoro-vinyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 5 ml DMSO and 0.25 ml water was added 4.98 mmol potassium fluoride and the mixture was heated at 120° C. for 2 h. The mixture was cooled to room temperature and then taken up in THF and washed sequentially with water and with brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (48% yield). MS (m/e): 246.3 ([M+H-Me2C═CH2]+, 100%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed sequentially with water and with brine
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-934e8f98ef8f4cbdb47750ca0f1b9aa1
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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