Lithium Hydroxide → 5-fluoro-2-(1H-pyrazol-5-yl)benzoic acid

HRID 1193109Notes

Reaction equation

HRID 1193109 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[Li+].[OH-]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[NH:16][N:15]=[CH:14][CH:13]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67086678methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate

Product 1

HCID 670868915-fluoro-2-(1H-pyrazol-5-yl)benzoic acidYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 5-fluoro-2-(1H-pyrazol-5-yl)benzoate (415 mg, 1.9 mmol) in EtOH (10 ml) was treated with 4.0 eq of LiOH and stirred and monitored for two hours the reaction was complete. Reaction was made to pH=5, and then the solution concentrated under reduced pressure, during which time a ppt formed. The solution was concentrated to minimum volume and cooled in ice, filtered and washed with ice water to give 5-fluoro-2-(1H-pyrazol-5-yl)benzoic acid (172 mg, 44%). 1H NMR (400 MHz, DMSO-d6): 13.03 (s, 1H), 7.71 (d, J=2.0 Hz, 1H), 7.67 (dd, J=8.3, 5.6 Hz, 1H), 7.37 (td, J=8.6, 2.9 Hz, 2H), 6.44 (d, J=2.2 Hz, 1H).

Workup

  1. customReaction
  2. concentrationthe solution concentrated under reduced pressure, during which time a ppt
  3. customformed
  4. concentrationThe solution was concentrated to minimum volume
  5. temperaturecooled in ice
  6. filtrationfiltered
  7. washwashed with ice water

Sources & evidence

ORD record
ord-599e2ed6e6254f5faae4e4a1ed9b904e
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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