Lithium Hydroxide → 4-(4-Chlorophenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoic acid

HRID 1620344Notes

Reaction equation

HRID 1620344 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:16]([C:17]3[C:18]([O:23][CH3:24])=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[C:9]([F:25])[CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:16]([C:17]3[C:18]([O:23][CH3:24])=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[C:9]([F:25])[CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66667452Methyl 4-(4-chlorophenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoate

Product 1

HCID 666667494-(4-Chlorophenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoic acidYield 126.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-chlorophenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoate (Preparation 31, 194 mg, 0.50 mmol) in THF (10 mL) was added aqueous lithium hydroxide solution (1M, 2.51 mL, 2.51 mmol) and the mixture stirred for 72 hours at room temperature under a nitrogen atmosphere. The reaction was then concentrated in vacuo to afford the title compound as a white solid (236 mg, 100%).

Workup

  1. concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record
ord-4dc89906df814f3db5e6e1b2cf7d137b
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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