Water → 6-Chloro-5-fluoropicolinic acid

HRID 509279Notes

Reaction equation

HRID 509279 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[CH:4][C:3]=1[F:12].O.O.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[F:12]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 46311229HCID 46311229, compound

Product 1

HCID 114126726-Chloro-5-fluoropicolinic acidYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-chloro-5-fluoropicolinate (1.35 g, 7.095 mmol) was dissolved in THF:H2O=6:1 (42 ml), followed by addition of lithium hydroxide monohydrate (596 mg, 14.19 mmol), and then the resulting mixture was stirred at room temperature for 3 hours. The resulting reaction liquid was concentrated under reduced pressure, dissolved by addition of distilled water (20 ml), acidified by slow addition of 1N aqueous HCl solution, and then extracted with 5% MeOH/MC (30 ml×2). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 1.04 g of white solid (80%).

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutiondissolved by addition of distilled water (20 ml)
  4. additionacidified by slow addition of 1N aqueous HCl solution
  5. extractionextracted with 5% MeOH/MC (30 ml×2)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfollowed by filtration, concentration, and vacuum
  8. customdrying

Sources & evidence

ORD record
ord-c5b83226f15349798a0bdb488d92a741
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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