Water → 2-Bromo-6-(2-ethoxyethoxy)pyridine

HRID 1359380Notes

Reaction equation

HRID 1359380 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH2:6][CH2:7][OH:8])[CH3:4].Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=1.O>CN(C)C=O>[Br:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:8][CH2:7][CH2:6][O:5][CH2:3][CH3:4])[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8076Glycol monoethyl etherHCID 122742,6-DibromopyridineHCID 24758Sodium hydride

Product 1

HCID 181824552-Bromo-6-(2-ethoxyethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1.7 g of 60% oily sodium hydride was suspended in 20 ml of N,N-dimethylformamide, followed by adding a solution of 10 ml of N,N-dimethylformamide containing 4.1 ml of 2-ethoxyethanol thereto with stirring under ice-cooling. After stirring for 20 minutes, a solution of 10 ml of N,N-dimethylformamide containing 5 g of 2,6-dibromopyridine was added thereto and the mixture was further stirred at room temperature for one hour. Then, water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 5% ethyl acetate/hexane as an eluent for separation and purification, to give 4.8 g of the target compound.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 20 minutes
  3. stirringthe mixture was further stirred at room temperature for one hour
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was further washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customfor separation and purification

Sources & evidence

ORD record
ord-6619913aeb7c496c9954f80c21a99b77
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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