Hydrochloric Acid → 4-((5-Chloro-6-methoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoic acid

HRID 512057Notes

Reaction equation

HRID 512057 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH2:11][C:12]2[C:22]([F:23])=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[C:14]([F:24])[CH:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[OH-].[Li+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:10][CH2:11][C:12]2[C:22]([F:23])=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[C:14]([F:24])[CH:13]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66667744Ethyl 4-((5-chloro-6-methoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoate

Product 1

HCID 680719214-((5-Chloro-6-methoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-((5-chloro-6-methoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoate (Preparation 32, 112 mg, 0.313 mmol) in THF (3 mL) was treated with aqueous lithium hydroxide (1 M, 1.6 mL, 1.60 mmol) and stirred at room temperature. After 2% hours the reaction mixture was acidified with aqueous hydrochloric acid solution (2 N, 15 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over magnesium sulfate and evaporated to afford the title compound as a white solid (100 mg, 97%).

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-8373f5db9b5044e2ac9ae01aa61fbbeb
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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