Methanol → Methyl 6-bromo-5-fluoropyridine-2-carboxylate

HRID 1523514Notes

Reaction equation

HRID 1523514 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[F:11].OS(O)(=O)=O.[CH3:17]O>C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:17])=[O:9])[CH:5]=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 534011946-Bromo-5-fluoropicolinic Acid

Product 1

HCID 46311204Methyl 6-bromo-5-fluoropyridine-2-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromo-5-fluoropicolinic acid (1.0 equiv.) in methanol (0.2 M) was added H2SO4 (4.2 equiv.) and the reaction was stirred at room temperature for two hours. Upon completion of the reaction as monitored by LC/MS, the reaction was diluted with ethyl acetate and quenched slowly with saturated aqueous NaHCO3. The reaction was poured into a separatory funnel and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate, filtered, and concentrated in vacuo to provide methyl 6-bromo-5-fluoropicolinate as a white solid (>99%). LC/MS=233.9/235.9 (M+H), Rt=0.69 min.

Workup

  1. customUpon completion of the reaction
  2. customquenched slowly with saturated aqueous NaHCO3
  3. additionThe reaction was poured into a separatory funnel
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0e1651a87da482494147b5b85059773
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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