Monobasic potassium phosphate → 4-Cyano-2,6-difluorobenzoic acid

HRID 875392Notes

Reaction equation

HRID 875392 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:12])[C:9]=1[CH:10]=[O:11])[C:5]#[N:6].P([O-])(O)(O)=[O:14].[K+].Cl([O-])=O.[Na+]>CS(C)=O.O>[C:5]([C:4]1[CH:3]=[C:2]([F:1])[C:9]([C:10]([OH:14])=[O:11])=[C:8]([F:12])[CH:7]=1)#[N:6]

Participants

6

Reactant 3

HCID 516951Monobasic potassium phosphateHCID 162182563,5-Difluoro-4-formylbenzonitrileHCID 23668197Sodium Chlorite

Product 1

HCID 445579334-Cyano-2,6-difluorobenzoic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 3,5-difluoro-4-formylbenzonitrile (0.2 g, 1.1 mmol) in dimethylsulfoxide (10 mL), were added a aqueous solution of potassium dihydrogen phosphate (0.41 g, 2.9 mmol in 0.4 mL of water), sodium chlorite (0.216 g, 2.3 mmol in 4 mL of water) in one lot at an ambient temperature. The resulting reaction mixture was stirred for about 1 hour. The reaction mass was diluted with water (100 mL). The aquoeus phase was extracted with ethyl acetate (3×100 mL). The combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated to afford 4-cyano-2,6-difluorobenzoic acid (200 mg, 91.32%).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe aquoeus phase was extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layer dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-78cae07fe37145718304a1ee3260039c
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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