2-Chloroquinoline → 2-Fluoroquinoline

HRID 514819Notes

Reaction equation

HRID 514819 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F-:12].[Cs+]>CS(C)=O.O>[F:12][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 119282-ChloroquinolineHCID 25953Cesium fluoride

Product 1

HCID 1605322-FluoroquinolineYield 75.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-chloroquinoline (4.9 g, 30 mmol) in 200 mL of anhydrous DMSO was added cesium fluoride (9.13 g, 60 mmol), and the resulting mixture was stirred at 130° C. overnight, when LC-MS showed completion of the reaction. After cooling, the reaction mixture was diluted with water, and then extracted with ethyl acetate. The organic layer was then washed with brine, dried over anhy. Na2SO4, and concentrated in vacuo. Column chromatography (6% EtOAc/PE) afforded 3.34 g of title compound. 1H NMR (CHLOROFORM-d) δ: 8.23 (d, J=8.6 Hz, 1H), 7.89 (d, J=8.6 Hz, 1H), 7.82-7.86 (m, 1H), 7.67 (d, J=8.5, 7.0, 1.5 Hz, 1H), 7.47-7.53 (m, 1H), 7.35 (d, J=8.6 Hz, 1H). LC-MS: m/z 148.2 (M+H)+

Workup

  1. customcompletion of the reaction
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was then washed with brine
  5. customdried over anhy
  6. concentrationNa2SO4, and concentrated in vacuo

Sources & evidence

ORD record
ord-08656c47317f47619f6a83d1b85e15ff
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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