Potassium Carbonate → 3-Fluoro-2-(3-fluoropyrrolidin-1-yl)benzaldehyde

HRID 1695949Notes

Reaction equation

HRID 1695949 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:11][C@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(OCC)(=O)C>[F:10][C:9]1[C:2]([N:14]2[CH2:15][CH2:16][CH:12]([F:11])[CH2:13]2)=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1376642,3-DifluorobenzaldehydeHCID 7016277(S)-3-fluoropyrrolidine

Product 1

HCID 766020043-Fluoro-2-(3-fluoropyrrolidin-1-yl)benzaldehydeYield 26.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2,3-Difluorobenzaldehyde (1.0 g, 7.037 mmol) was taken up in dry dioxane (20 ml) in a tube and (S)-3-fluoropyrrolidine (627.1 mg, 7.037 mmol) and K2CO3 (676.4 mg, 10.56 mmol) were added and the mixture refluxed overnight. The reaction mixture was diluted with ethyl acetate, filtered, concentrated to dryness and purified on an ISCO system eluting with Hexane/ethyl acetate (10-100) to give 400 mg of 3-fluoro-2-(3-fluoropyrrolidin-1-yl) benzaldehyde.

Workup

  1. temperaturethe mixture refluxed overnight
  2. filtrationfiltered
  3. concentrationconcentrated to dryness
  4. custompurified on an ISCO system
  5. washeluting with Hexane/ethyl acetate (10-100)

Sources & evidence

ORD record
ord-2df28bcfe0b84cbf81347d918b414fcf
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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