2-Methoxyethanol → 3-Bromo-5-(2-methoxyethoxy)pyridine

HRID 1175120Notes

Reaction equation

HRID 1175120 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Br[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1>CN(C=O)C>[Br:15][C:13]1[CH:14]=[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:10]=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

Product 1

HCID 107759113-Bromo-5-(2-methoxyethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Methoxyethanol (2.7 ml; 33.8 mmol) is added dropwise to a suspension of NaH (55% suspension; 1.62 g; 37.14 mmol) in DMF (60 ml). After stirring for 30 minutes, 3,5-dibromopyridine (4.0 g; 16.88 mmol) is introduced and the mixture heated to 50° C. for 1 hour. The reaction mixture is poured on water and extracted with ethyl acetate three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness. Chromatography (SiO2; Hexanes/acetone 85:15) yields the title compound as yellow solid.

Workup

  1. additionThe reaction mixture is poured on water
  2. extractionextracted with ethyl acetate three times
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-f9ef88e62ba743778f32c27007a1e0f8
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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