Methanol → Methyl 5-bromopyridine-2-carboxylate

HRID 509594Notes

Reaction equation

HRID 509594 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:15])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 7016458Methyl 5-bromopyridine-2-carboxylate

Procedure

To a 100 mL round bottle flask with 5-bromopicolinic acid (7.0 g, 0.035 mol) in methanol (80 mL) was added thionyl chloride (3.0 mL) dropwise at ambient temperature. After the addition the reaction mixture was heated to reflux for 3 h. Methanol was removed and ethyl acetate (100 mL) was added to the residue and was adjusted pH to 7.0 by addition of sodium bicarbonate solution. The organic phase was separated and dried over sodium sulfate. The organic solvent was removed and methyl 5-bromopicolinate 2 was obtained as white solid which was used for the next step reaction without further purification. Yield: 6.57 g, 86.9%.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 3 h
  4. customMethanol was removed
  5. additionethyl acetate (100 mL) was added to the residue
  6. additionwas adjusted pH to 7.0 by addition of sodium bicarbonate solution
  7. customThe organic phase was separated
  8. dry with materialdried over sodium sulfate
  9. customThe organic solvent was removed

Sources & evidence

ORD record
ord-813a020889c341e69278bc723a2a8a0b
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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