Reacción #2439924

ord-3dc347428eed4c3f9d01dfe21c8e117c

Ecuación de reacción

O=C(O)c1cncc(Br)c1
3-bromo-5-pyridine-carboxylic acid
O=S(=O)(O)O
H2SO4
CCO
EtOH
CCOC(=O)c1cncc(Br)c1
3-bromo-5-pyridine-carboxylic acid ethyl ester

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas refluxed for 6 hrs
  2. 2
    TemperaturaAfter cooling
  3. 3
    Otrothe solvent was removed by evaporation in vacuo
  4. 4
    workup.ADDITIONThe residue as diluted with H2O (100 ml)
  5. 5
    Extracciónextracted with ether (4×100 ml)
  6. 6
    LavadoThe combined organic extracts were washed with saturated NaCl
  7. 7
    Secadodried over Na2SO4
  8. 8
    FiltraciónFiltration and concentration in vacuo of the filtrate

Procedimiento

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 as 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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE041425E1uspto-grants-2010_07