Propargyl bromide → HCID 21467243, compound

HRID 1939248Notes

Reaction equation

HRID 1939248 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH2:11](Br)[C:12]#[CH:13]>C1COCC1>[Br:1][C:2]1[C:7]([O:8][CH2:13][C:12]#[CH:11])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydride

Product 1

HCID 21467243HCID 21467243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-3-hydroxypyridine (10 g) in dry THF (100 ml) was treated with 1 equivalent of sodium hydride (80% in oil) (1.72 g) and stirred at room temperature under nitrogen for 0.75 hours. Propargyl bromide (80% in toluene) (19.2 ml) was added and the mixture was heated under reflux for 88 hours. After cooling, the solvent was evaporated under reduced pressure and the residue partitioned between 5% aqueous NaOH and EtOAc. The organic layer was removed, dried (Na2SO4) and concentrated in vacuo to give a pale yellow gum. This was purified by column chromatography on silica using dichloromethane as eluant to give 2-bromo-3-propargyloxypyridine as an off white solid 6 g.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 88 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue partitioned between 5% aqueous NaOH and EtOAc
  6. customThe organic layer was removed
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto give a pale yellow gum
  10. customThis was purified by column chromatography on silica

Sources & evidence

ORD record
ord-5622e1bedb504dbb97a2850eef5ef5e6
Source dataset
uspto-grants-1997_12
Patent number
US05696129

Reaction notes

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