Lithium Hydroxide → 6-(2,6-Difluoro-4-methoxyphenyl)-5-fluoropicolinic acid

HRID 879096Notes

Reaction equation

HRID 879096 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:13][C:12]=1[F:21].[Li+].[OH-]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59226460Methyl 6-(2,6-difluoro-4-methoxyphenyl)-5-fluoropicolinate

Product 1

HCID 592264666-(2,6-Difluoro-4-methoxyphenyl)-5-fluoropicolinic acidYield 84%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(2,6-difluoro-4-methoxyphenyl)-5-fluoropicolinate (1.0 equiv.) in THF/MeOH (2:1, 0.09 M) was added LiOH (1.5 equiv.) and the reaction was stirred at room temperature for 1 hour. The solution was quenched with 1N HCl, extracted with ethyl acetate, washed with brine, dried with sodium sulfate, filtered and concentrated to give 6-(2,6-difluoro-4-methoxyphenyl)-5-fluoropicolinic acid in 84% yield. LC/MS=284.1 (M+H), Rt=0.76 min.

Workup

  1. customThe solution was quenched with 1N HCl
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-831f44043b824cce821e9134a9df9fff
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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