Ethanol → Ethyl 5-bromopyridine-3-carboxylate

HRID 2244203Notes

Reaction equation

HRID 2244203 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[CH2:16]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=1)[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 887075-Bromonicotinic acid

Product 1

HCID 140785Ethyl 5-bromopyridine-3-carboxylate

Procedure

A solution of 5-bromonicotinic acid (5.15 g, 25.5 mmol) in ethanol (100 mL) containing 1 mL of concentrated sulfuric acid was refluxed for 18 hours. The solvent was removed under reduced pressure and the residue basified with saturated aqueous sodium bicarbonate. The solution was then extracted three times with ether. The organics were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the tittle compound (5.29 g) as an off white solid.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. extractionThe solution was then extracted three times with ether
  4. dry with materialThe organics were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68a9bc785589431f8baef4b7f252e9c9
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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