Ethanol → Ethyl 5-bromopyridine-3-carboxylate

HRID 2288626Notes

Reaction equation

HRID 2288626 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1.OS(O)(=O)=O.[CH3:16][CH2:17]O>>[CH2:16]([O:9][C:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=1)=[O:10])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 887075-Bromonicotinic acid

Product 1

HCID 140785Ethyl 5-bromopyridine-3-carboxylate

Procedure

A stirred mixture of 3-bromo-5-pyridine-carboxylic acid (10.1 g, 50 mmol) and H2SO4 (1.5 ml) in EtOH (150 ml) was refluxed for 6 hrs. After cooling, the solvent was removed by evaporation in vacuo. The residue was diluted with H2O (100 ml), basified with 5% NaHCO3 (aq) solution and extracted with ether (4×100 ml). The combined organic extracts were washed with saturated NaCl and dried over Na2SO4. Filtration and concentration in vacuo of the filtrate yielded 3-bromo-5-pyridine-carboxylic acid ethyl ester as an oil that solidified on standing: (9.8 g, 85%).

Workup

  1. temperaturewas refluxed for 6 hrs
  2. temperatureAfter cooling
  3. customthe solvent was removed by evaporation in vacuo
  4. additionThe residue was diluted with H2O (100 ml)
  5. extractionextracted with ether (4×100 ml)
  6. washThe combined organic extracts were washed with saturated NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration and concentration in vacuo of the filtrate

Sources & evidence

ORD record
ord-61f2eea3339a40019ae2e4e6de7f7e5c
Source dataset
uspto-grants-2000_07
Patent number
US06090812

Reaction notes

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