Sulfuric Acid → Methyl 6-bromopyridine-2-carboxylate

HRID 2233902Notes

Reaction equation

HRID 2233902 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]COC(C)=O.C(=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:16])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 5939196-Bromopyridine-2-carboxylic acid

Product 1

HCID 16217886Methyl 6-bromopyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Bromopicolinic acid (411 mg, 2.03 mmol) was slurried in anhydrous MeOH (6 ml). Concentrated sulfuric acid (0.3 ml) was added and the resulting solution was stirred at room temperature for approximately 3 h. EtOAc was added, followed by a saturated solution of sodium bicarbonate. The phases were separated, and the organic phase was washed with water, dried over MgSO4, and concentrated to dryness. The crude ester (313 mg) was used without further purification.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe crude ester (313 mg) was used without further purification

Sources & evidence

ORD record
ord-910051220d154479a110ee50476ffdd5
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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