2-Chloroquinoline → 2-Fluoroquinoline

HRID 2202355Notes

Reaction equation

HRID 2202355 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-7fa5a5c62bad42cfa1a32404c143e238
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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