Sodium Chloride → 5-fluoropyridine-2-carboxylic Acid

HRID 1772803Notes

Reaction equation

HRID 1772803 reaction equation
OP([O-])(O)=O.[K+].[F:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[N:12][CH:13]=1.Cl([O-])=[O:17].[Na+].[Na+].[Cl-]>O.CS(C)=O.CCOC(C)=O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([OH:17])=[O:15])=[N:12][CH:13]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 516951Monobasic potassium phosphateHCID 103516975-Fluoropyridine-2-carboxaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 27628765-fluoropyridine-2-carboxylic AcidYield 65.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium phosphate monobasic (1.4 g, 10 mmol) in water (10 mL) was added to a solution of 5-fluoropyridine-2-carbaldehyde (0.50 g, 4.0 mmol, Frontier) in DMSO (10 mL). Sodium chlorite (0.9 g, 0.008 mol) in water (10 mL) was added, and the reaction continued for 1 hour. The mixture was saturated with NaCl, then diluted with EtOAc. The organic layer was further washed with brine, dried over sodium sulfate and concentrated to afford product (370 mg, 65%). 1H NMR (400 MHz, CDCl3): δ□8.50 (d, 1H), 8.29 (ddd, 1H), 7.66 (ddd, 1H); LCMS (M+H)+: 142.0.

Workup

  1. washThe organic layer was further washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bb5d6f8b8f1d4c54a30af2cf96b62daf
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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