2-Methoxyethanol → 5-Bromo-2-(2-methoxyethoxy)pyridine

HRID 2170032Notes

Reaction equation

HRID 2170032 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].[Br:12][C:13]1[CH:14]=[CH:15][C:16](Cl)=[N:17][CH:18]=1>O1CCOCC1.[Cl-].[Na+].O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 80192-MethoxyethanolHCID 27344145-Bromo-2-chloropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 225027175-Bromo-2-(2-methoxyethoxy)pyridineYield 73%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Methoxyethanol (5.12 mL, 85.0 mmol) was dissolved in 1,4-dioxane (125 ml). Potassium tert-butoxide (7.00 g, 62.4 mmol) was added under N2. The mixture was stirred for 10 minutes. 5-Bromo-2-chloropyridine (10.0 g, 52.0 mmol) was added and the resulting mixture was refluxed for 2 hours. The mixture was poured into brine and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated to dryness. Purification by flash chromatography (silica, heptanes/EtOAc 4:1) gave the title compound as a colorless oil (8.74 g, 73%) sufficiently pure for the next step.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customPurification by flash chromatography (silica, heptanes/EtOAc 4:1)

Sources & evidence

ORD record
ord-6c2d02e6e6eb48fe8b2c539479d715a1
Source dataset
uspto-grants-2015_06
Patent number
US09050327B2

Reaction notes

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