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

HRID 1952777Notes

Reaction equation

HRID 1952777 reaction equation
[Na].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1.C(=O)([O-])O.[Na+].[CH3:15][O:16][CH2:17][CH2:18][OH:19]>>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([O:19][CH2:18][CH2:17][O:16][CH3:15])=[N:4][CH:5]=1

Participants

5

Reactant 4

HCID 80192-MethoxyethanolHCID 693532,5-DibromopyridineHCID 516892Sodium BicarbonateHCID 5360545Sodium

Product 1

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

Conditions

Temperature
90 °C

Procedure

1.1 g sodium and 2.5 g 2,5-dibromo-pyridine are added to 50 ml 2-methoxy-ethanol. The reaction mixture is heated to 90° C. and stirred for a further 2.5 hrs, then poured onto 75 ml of a saturated sodiumhydrogen carbonate solution and extracted three times with methylenchloride. The organic phases are combined, dried over sodium sulphate and concentrated and the residue is destilled. 2.2 g 5-Bromo-2-(2-methoxy-ethoxy)-pyridine are obtained., bp. 135° C./0.1 mbar MS (EI): 231 (M).

Workup

  1. extractionextracted three times with methylenchloride
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-473c847aa3e44f18bf687550d890c97f
Source dataset
uspto-grants-2000_09
Patent number
US06114330

Reaction notes

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