Ethanol → Ethyl 5-bromopyridine-3-carboxylate

HRID 910283Notes

Reaction equation

HRID 910283 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].[CH2:15](O)[CH3:16]>>[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([O:13][CH2:15][CH3:16])=[O:12]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 887075-Bromonicotinic acid

Product 1

HCID 140785Ethyl 5-bromopyridine-3-carboxylateYield 82%

Procedure

20 ml (27 mmol) of thionyl chloride are added dropwise, at room temperature, to a solution of 10 g (49 mmol) of 5-bromonicotinic acid in 250 ml of ethanol. The reaction medium is stirred at room temperature for 4 days and then evaporated under vacuum. The residue is taken up in dichloromethane and washed with aqueous sodium carbonate solution. The organic phase is dried over sodium sulfate, filtered and evaporated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 9 g (82%) of ethyl 5-bromonicotinate are obtained.

Workup

  1. customevaporated under vacuum
  2. washwashed with aqueous sodium carbonate solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 7/3 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-806042bbceef4a33b264fa27491e11d9
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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