Lithium Hydroxide → 2,5-Difluoro-4-[(3-methoxyphenoxy)methyl]benzoic acid

HRID 508438Notes

Reaction equation

HRID 508438 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:9]([F:22])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+]>C1COCC1>[F:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:9]([F:22])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86682556Methyl 2,5-difluoro-4-[(3-methoxyphenoxy)methyl]benzoate

Product 1

HCID 666690642,5-Difluoro-4-[(3-methoxyphenoxy)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2,5-difluoro-4-[(3-methoxyphenoxy)methyl]benzoate (Preparation 28, 441 mg, 1.4 mmol) in THF (10 mL) was added aqueous lithium hydroxide (1 M, 1.6 mL) and the reaction mixture stirred under nitrogen at room temperature. After 5 hours, the reaction was evaporated in vacuo and the residue suspended in a water/EtOAc mixture (20 mL), acidified with a few drops of aqueous 1 M hydrochloric acid. The layers were separated and the aqueous layer further extracted with EtOAc (10 mL). The combined organics were dried over magnesium sulphate and concentrated in vacuo to yield the title compound as an off white solid which was used in the next step without further purification (371 mg, 88%):

Workup

  1. customthe reaction was evaporated in vacuo
  2. customThe layers were separated
  3. extractionthe aqueous layer further extracted with EtOAc (10 mL)
  4. dry with materialThe combined organics were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dfaf7d7303d4379ba254c94a956ade9
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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