Ethanol → Ethyl 2-(5-bromopyridin-3-yl)acetate

HRID 1913177Notes

Reaction equation

HRID 1913177 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[N:6][CH:7]=1.[CH2:12](O)[CH3:13]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

15 drops of concentrated sulfuric acid are added to 5.0 g (23.1 mmol) of (5-bromopyridin-3-yl)acetic acid in 30 ml of ethanol, and the mixture is heated under reflux for 16 h. After cooling to RT, the mixture is concentrated under reduced pressure and the residue is taken up in ethyl acetate and washed with semiconcentrated sodium bicarbonate solution. The organic phase is dried over sodium sulfate, filtered and concentrated under reduced pressure.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 h
  3. concentrationthe mixture is concentrated under reduced pressure
  4. washwashed with semiconcentrated sodium bicarbonate solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2372085b2410441f991f2c113a5b69e0
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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