Hydrochloric Acid → 5-Bromo-2-fluoropyridine-3-carboxylic acid

HRID 1986094Notes

Reaction equation

HRID 1986094 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 45588056Methyl 5-bromo-2-fluoropyridine-3-carboxylate

Product 1

HCID 247213715-Bromo-2-fluoropyridine-3-carboxylic acidYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromo-2-fluoronicotinate (90 mg, 0.38 mmol) in 2 mL of THF was added 1N NaOH (1.0 mL, 1.0 mmol) at room temperature. The reaction was stirred at room temperature for 2 h before it was neutralized by 1.0 mL of 1N HCl. The solution was then concentrated under reduced pressure and the residue was purified on preparative (RP) HPLC to provide 5-Bromo-2-fluoronicotinic acid (55 mg).

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customthe residue was purified on preparative (RP) HPLC

Sources & evidence

ORD record
ord-912e63f2857447f3b51b9f9b06087e95
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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