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

HRID 2080690Notes

Reaction equation

HRID 2080690 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

73 ml of methoxymethyl chloride was added to a tetrahydrofuran (1.3 L) solution of 129 g of the obtained 6-bromo-3-pyridinol, and 32 g of sodium hydride (with 30% liquid paraffin added thereto) was added to it under so control that the inner temperature could not exceed −110° C. Water was added to it, 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 through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9.1 to 8/1) to obtain 105 g of the entitled compound as a colorless oil.

Workup

  1. additionadded
  2. addition) was added to it under so control that the inner temperature could not
  3. customexceed −110° C
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with saturated saline water
  6. customAfter dried
  7. customthe solvent was evaporated away under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9.1 to 8/1)

Sources & evidence

ORD record
ord-5837e7589c454ce99d9b7ea8f029d356
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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