Chloromethyl Methyl Ether → 2-Bromo-5-(methoxymethoxy)pyridine

HRID 1671658Notes

Reaction equation

HRID 1671658 reaction equation
[CH3:1][O:2][CH2:3]Cl.O1CCCC1.[Br:10][C:11]1[N:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[H-].[Na+]>O>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:1][O:2][CH3:3])=[CH:15][N:16]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 574336662-Bromo-5-(methoxymethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methoxymethyl chloride (73 ml) was added to a tetrahydrofuran (1.3 L) solution of 6-bromo-3-pyridinol (129 g) thus obtained, and sodium hydride (40% liquid paraffin added, 32 g) was added to it in such a manner that the inner temperature could not be above −10° C. Water was added, and extracted with ethyl acetate, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and this was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 8/1) to obtain the entitled compound as a colorless oily substance.

Workup

  1. customthus obtained
  2. custombe above −10° C
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with saturated saline water
  5. customAfter dried
  6. customthe solvent was evaporated away under reduced pressure
  7. customthis was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 8/1)
  8. customto obtain the entitled compound as a colorless oily substance

Sources & evidence

ORD record
ord-ce13067097bb4ae8a6a83cfa364587de
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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