Hydrochloric Acid → 5-Bromo-3-fluoropicolinic acid hydrochloride

HRID 873317Notes

Reaction equation

HRID 873317 reaction equation
[F:1][C:2]1[C:3]([C:9](N)=[O:10])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[OH-:12].[Na+].[ClH:14]>>[ClH:14].[F:1][C:2]1[C:3]([C:9]([OH:10])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 210758715-Bromo-3-fluoropyridine-2-carboxamide

Product 1

HCID 709788255-Bromo-3-fluoropicolinic acid hydrochloride

Procedure

A solution of 3-fluoro-5-bromopyridine-2-carboxamide (1.44 g, 6.5 mmol) in conc HCl (aq) (17 mL) was heated to 120° C. for 1.5 h. The reaction was cooled in an ice bath and 48% NaOH was added to slowly until the pH was 5. The solvent was removed in vacuo and toluene (25 mL) was added and then removed in vacuo. The resulting solid was extracted with 4:6 methanol/DCM (×2) and the combined extracts evaporated in vacuo to give crude 3-fluoro-5-bromopyridine carboxylic acid hydrochloride which was used directly without further purification.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customThe solvent was removed in vacuo and toluene (25 mL)
  3. additionwas added
  4. customremoved in vacuo
  5. extractionThe resulting solid was extracted with 4:6 methanol/DCM (×2)
  6. customthe combined extracts evaporated in vacuo

Sources & evidence

ORD record
ord-52351b74295d42029910175b67b831a4
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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