1-Bromopropane → 2-Bromo-5-propoxypyridine

HRID 330766Notes

Reaction equation

HRID 330766 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.Br[CH2:10][CH2:11][CH3:12].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH3:12])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 665213962-Bromo-5-propoxypyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.0 g (57.5 mmol) 2-bromo-5-hydroxypyridine, 28.3 g (230 mmol) 1-bromopropane and 19.9 g (143.7 mmol) K2CO3 are added to 1 L ACN and stirred at reflux over night. Afterwards the reaction is quenched by the addition of water and extracted with TBME. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc).

Workup

  1. temperatureat reflux over night
  2. customAfterwards the reaction is quenched by the addition of water
  3. extractionextracted with TBME
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc)

Sources & evidence

ORD record
ord-9d2bb70262ba419b9dad22782050253a
Source dataset
uspto-grants-2014_11
Patent number
US08877741B2

Reaction notes

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