Ethanol → Ethyl 2,5-dibromoisonicotinate

HRID 2047587Notes

Reaction equation

HRID 2047587 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([Br:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([Br:11])=[CH:9][N:10]=1)[C:5]([O:7][CH2:17][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 263436962,5-Dibromopyridine-4-carboxylic acid

Product 1

HCID 46311329Ethyl 2,5-dibromoisonicotinate

Procedure

A solution of 2,5-dibromoisonicotinic acid (1-1, 5 g, 17.80 mmol) and sulfuric acid (1.23 mL, 23.1 mmol) in ethanol (100 mL) was heated to reflux overnight. After reducing the volume of ethanol by rotary evaporation to approximately ¼ of it's original volume, the crude reaction mixture was partitioned between 2M sodium carbonate solution and EtOAc, separating layers and washing the organic layer with saturated sodium bicarbonate solution and brine. This solution was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (0 to 50% EtOAc in hexanes) to afford the product (1-2) as a dark oil. ESI+MS [M]+C8H7Br2NO2=308.0.

Workup

  1. temperatureto reflux overnight
  2. customby rotary evaporation to approximately ¼ of it's original volume
  3. customthe crude reaction mixture
  4. customwas partitioned between 2M sodium carbonate solution and EtOAc
  5. customseparating layers
  6. washwashing the organic layer with saturated sodium bicarbonate solution and brine
  7. dry with materialThis solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by normal phase column chromatography (0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-179c8600570a4667b0afd296c402cf80
Source dataset
uspto-grants-2013_11
Patent number
US08592457B2

Reaction notes

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