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

HRID 1524938Notes

Reaction equation

HRID 1524938 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 reactions was then concentrated to minimum volume and cooled in ice, then filtered and washed with ice water to give 5-fluoro-2-(1H-pyrazol-5-yl)benzoic acid (172 mg, 44% yield). 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 reactions was then concentrated to minimum volume
  5. temperaturecooled in ice
  6. filtrationfiltered
  7. washwashed with ice water

Sources & evidence

ORD record
ord-30d8283c6cea4ebe8b00d902e6fc31c1
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

Loading…