Dimethyl Sulfoxide → 3-(4-Fluorobenzenesulfonyl)pyridine-2-carbaldehyde

HRID 1944394Notes

Reaction equation

HRID 1944394 reaction equation
F[C:2]1[C:3]([CH:8]=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[Na+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.CS(C)=O>O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:2]2[C:3]([CH:8]=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 113440173-Fluoro-2-pyridinecarboxaldehydeHCID 236662204-fluorobenzenesulfinic acid sodium salt

Product 1

HCID 866521843-(4-Fluorobenzenesulfonyl)pyridine-2-carbaldehydeYield 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-fluoropyridine-2-carbaldehyde (0.70 g), 4-fluorobenzenesulfinic acid sodium salt (1.1 g) and dimethyl sulfoxide (7.0 mL) was stirred at 100° C. for 18 hours. The mixture was cooled to room temperature, diluted with water (20 mL), and the resulting precipitate was removed by filtration. The filtrate was extracted with ethyl acetate, and the combined organic extract was washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford the title compound as a pale yellow oil (0.67 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe resulting precipitate was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. extractionthe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-38ba5b692de14e688586b3ca5cfcc930
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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