Ethanol → Ethyl 5-bromopicolinate

HRID 450495Notes

Reaction equation

HRID 450495 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:16](O)[CH3:17].C(=O)([O-])O.[Na+]>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:16][CH3:17])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 6085445-Bromopyridine-2-carboxylic acid

Product 1

HCID 12686158Ethyl 5-bromopicolinateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-bromopyridine-2-carboxylic acid (35.0 g, 173 mmol), sulfuric acid (12.0 mL) and ethanol (300 mL) was stirred at 75° C. for 2 hr. After cooling to 0° C., the mixture was neutralized with sodium hydrogen carbonate and diluted with water (150 mL). Ethanol was evaporated under reduced pressure, and the residue was extracted with ethyl acetate (300 mL). The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained solid was collected by filtration, washed with hexane, and dried to give the title compound (34.5 g, 86%) as a white solid.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customEthanol was evaporated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate (300 mL)
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe obtained solid was collected by filtration
  8. washwashed with hexane
  9. customdried

Sources & evidence

ORD record
ord-fa107fcb00224dfa838ed7adb5159fbd
Source dataset
uspto-grants-2013_07
Patent number
US08486965B2

Reaction notes

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