2-(Benzyloxy) ethanol → 2-(2-(Benzyloxy)ethoxy)-6-bromopyridine

HRID 1636177Notes

Reaction equation

HRID 1636177 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[N:16]=1>C1(C)C=CC=CC=1.O>[CH2:3]([O:10][CH2:11][CH2:12][O:13][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([Br:14])[N:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 121412-(Benzyloxy) ethanolHCID 122742,6-DibromopyridineHCID 24758Sodium hydride

Product 1

HCID 186738282-(2-(Benzyloxy)ethoxy)-6-bromopyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium hydride (900 mg, 60% dispersion in mineral oil, 22.5 mmol) was added portionwise to an ice-cold solution of 2-(benzyloxy)ethanol (3.0 g, 20.0 mmol) in toluene (100 ml), and the solution stirred for 30 minutes. 2,6-Dibromopyridine (4.75 g, 20.0 mmol) was added, and the reaction heated under reflux for 2 hours. The cooled mixture was diluted with water (100 ml), and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo to give the title compound as a yellow oil, (quantitative).

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-660881e9aa194da2a4c87925444ad01e
Source dataset
uspto-grants-2003_01
Patent number
US06511993B1

Reaction notes

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