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

HRID 330831Notes

Reaction equation

HRID 330831 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].C1COCC1.Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1>C([O-])(O)=O.[Na+]>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 80192-MethoxyethanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 225027175-Bromo-2-(2-methoxyethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

0.25 mL 2-methoxyethanol (3.17 mmol) are added to a mixture of 80 mg (3.17 mmol) sodium hydride and 5 mL THF. The mixture is stirred at rt for 10 min. Subsequently, 500 mg (2.11 mmol) 2,5-dibromopyridine are added and the mixture is stirred for 5 h at 75° C. After that time, the reaction mixture is diluted with sat. aq. NaHCO3 solution and extracted with EtOAc. The organic layer is dried over magnesium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc 85/15).

Workup

  1. stirringthe mixture is stirred for 5 h at 75° C
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried over magnesium sulphate
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc 85/15)

Sources & evidence

ORD record
ord-fef4f21f5ac54b9189cbdb31ce4a5c00
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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