Hydrochloric Acid → 5-(2,5-Difluorobenzyl)-1,2,4-oxadiazole-3-carboxylic acid

HRID 58575Notes

Reaction equation

HRID 58575 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:5]=1[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[N:8]=1.Cl>C(O)C>[F:3][C:4]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:5]=1[CH2:6][C:7]1[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66832131Ethyl 5-(2,5-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate

Product 1

HCID 668318635-(2,5-Difluorobenzyl)-1,2,4-oxadiazole-3-carboxylic acidYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium hydroxide 1M (2 mL, 2 mmol) was added to a mixture of ethyl 5-(2,5-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylate (0.150 g; 0.559 mmol) in ethanol (1 mL) and the reaction was stirred at room temperature for 1 hour. The pH of the solution was adjusted to 1 by addition of a solution of hydrochloric acid 6N. The precipitate was collected by filtration and dried under reduced pressure to afford 0.124 g (92%) of 5-(2,5-difluorobenzyl)-1,2,4-oxadiazole-3-carboxylic acid as a white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-5441b82115fb426595532047c77fab6d
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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