Ethyl Bromide → 2-Bromo-5-ethoxypyridine

HRID 76129

Reaction equation

HRID 76129 reaction equation
Br[CH2:2][CH3:3].C([O-])([O-])=O.[K+].[K+].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][N:12]=1>C(#N)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][CH3:3])=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 234368922-Bromo-5-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.51 g (22.99 mmol) 1-bromoethane and 1.99 g (14.37 mmol) K2CO3 are added to a mixture of 1.0 g (5.75 mmol) 2-bromo-5-hydroxypyridine in 100 mL ACN. The mixture is stirred at reflux over night. Then the reaction mixture is poured onto water and extracted with TBME. The organic layer is dried with Na2SO4 and the solvent is removed under vacuo. The residue is purified by column chromatography (silica gel, PE/EtOAC 1/1).

Workup

  1. temperatureat reflux over night
  2. additionThen the reaction mixture is poured onto water
  3. extractionextracted with TBME
  4. dry with materialThe organic layer is dried with Na2SO4
  5. customthe solvent is removed under vacuo
  6. customThe residue is purified by column chromatography (silica gel, PE/EtOAC 1/1)

Sources & evidence

ORD record
ord-36769e8c1de347da8d1796f0a24d3516
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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