Lithium Hydroxide → HCID 66652225, compound

HRID 705185Notes

Reaction equation

HRID 705185 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[N:15]=[C:14]([C:16]([O:18]C)=[O:17])[CH:13]=[CH:12][C:11]=1[F:20].[Li+].[OH-]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:10]1[N:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:11]=1[F:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66652482Methyl 6-(2,6-difluoro-4-methylphenyl)-5-fluoropicolinate

Product 1

HCID 66652225HCID 66652225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(2,6-difluoro-4-methylphenyl)-5-fluoropicolinate (1.0 eq) in THF (0.1M) was added LiOH (5.5 eq, 2M) and allowed to stir at room temperature for 4 hrs. The volatiles were removed in vacuo, and the residual aqueous was acidified with 2M HCl to pH 4. The precipitate was filtered and dried to yield 6-(2,6-difluoro-4-methylphenyl)-5-fluoropicolinic acid as a light yellow solid in 73.5%. LCMS (m/z): 268.0 (MH+), Rt=0.76 min.

Workup

  1. customThe volatiles were removed in vacuo
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-cfc3a413af264885b7f1f710ada77de0
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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