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

HRID 889292Notes

Reaction equation

HRID 889292 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.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.00 g (4.63 mmol) (5-bromopyridin-3-yl)acetic acid are initially introduced into 20 ml ethanol, 2 ml conc. sulfuric acid are added and the mixture is stirred under reflux overnight. The reaction solution is introduced on to a mixture of 100 ml saturated sodium bicarbonate solution and 100 ml ethyl acetate, while stirring, and the aqueous phase is extracted with ethyl acetate (three times with 50 ml each time). The combined organic phases are dried over sodium sulfate, filtered and concentrated and the residue is freed from solvent residues overnight in vacuo.

Workup

  1. additionare added
  2. temperatureunder reflux overnight
  3. stirringwhile stirring
  4. extractionthe aqueous phase is extracted with ethyl acetate (three times with 50 ml each time)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customis freed from solvent residues overnight in vacuo

Sources & evidence

ORD record
ord-bbf3a790f6884c998200d5171d3ae057
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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