Ethyl Bromide → 2-Bromo-5-ethoxypyridine

HRID 40567

Reaction equation

HRID 40567 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-52b68b2543574d2f8bafa4e5182d8539
Source dataset
uspto-grants-2013_09
Patent number
US08530460B2

Linked notes

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