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

HRID 705182Notes

Reaction equation

HRID 705182 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-3b3df2e6a1734ea68617d369eb89923c
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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