Methanol → Methyl 3-bromo-2-pyridinecarboxylate

HRID 1658317Notes

Reaction equation

HRID 1658317 reaction equation
[Br:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.B(F)(F)F.[CH3:15]O>>[Br:1][C:2]1[C:3]([C:8]([O:10][CH3:15])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6356Boron trifluorideHCID 20501293-Bromopyridine-2-carboxylic Acid

Product 1

HCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

Procedure

3-Bromopicolinic acid (5 g.) is stirred and refluxed under nitrogen with 40 ml. of 14% boron trifluoride in methanol. the solution is cooled and the methanol is evaporated. The residue is dissolved in chloroform. The chloroform extracts are washed with 5% aqueous sodium bicarbonate solution and water, then the organic solution is dried and evaporated. The residue is recrystallized from cyclohexane to give methyl 3-bromopicolinate, m.p. 34°-36°C.

Workup

  1. temperaturerefluxed under nitrogen with 40 ml
  2. temperaturethe solution is cooled
  3. customthe methanol is evaporated
  4. dissolutionThe residue is dissolved in chloroform
  5. washThe chloroform extracts are washed with 5% aqueous sodium bicarbonate solution and water
  6. customthe organic solution is dried
  7. customevaporated
  8. customThe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-bc9338df266344aabb5256c10bc9c864
Source dataset
uspto-grants-1976_06
Patent number
US03963733

Reaction notes

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