Methanol → Methyl 3-bromo-2-pyridinecarboxylate

HRID 1750483Notes

Reaction equation

HRID 1750483 reaction equation
[Br:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:16]O>C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:3]([C:8]([O:10][CH3:16])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20501293-Bromopyridine-2-carboxylic Acid

Product 1

HCID 12828946Methyl 3-bromo-2-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-bromopyridine-2-carboxylic acid (CAS number 30683-23-9; 2.0 g, 9.90 mmol) in methanol (15 ml) was added concentrated H2SO4 (3 ml) and the reaction mixture was refluxed for 2 hours. The reaction was diluted with a saturated solution of sodium bicarbonate and extracted with ethyl acetate (3×75 ml). The organics were washed with water (50 ml), brine (20 ml), dried over sodium sulfate and concentrated in vacuo to afford the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate (3×75 ml)
  3. washThe organics were washed with water (50 ml), brine (20 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2463a31c48984b82bb4e4e879820ac53
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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