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

HRID 1715316Notes

Reaction equation

HRID 1715316 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 the obtained 6-bromo-3-pyridinol (129 g), and sodium hydride (30% liquid paraffin added) (32 g) was added at an inner temperature not to be over −10° C. Water was added, 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 the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 8/1) to obtain the entitled compound (105 g) as a colorless oil.

Workup

  1. additionwas added at an inner temperature not
  2. customto be over −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. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 8/1)

Sources & evidence

ORD record
ord-88871bdb48544c71aa5100353f1e1039
Source dataset
uspto-grants-2010_09
Patent number
US07799820B2

Reaction notes

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