Chloromethyl Methyl Ether → HCID 86649795, compound

HRID 1967551Notes

Reaction equation

HRID 1967551 reaction equation
[CH3:1][O:2][CH2:3]Cl.C(=O)([O-])[O-].[K+].[K+].[Br:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[N:13]=1>CC(C)=O>[Br:11][C:12]1[C:17]([O:18][CH2:1][O:2][CH3:3])=[CH:16][CH:15]=[C:14]([N+:19]([O-:21])=[O:20])[N:13]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 22615159HCID 22615159, compound

Product 1

HCID 86649795HCID 86649795, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

With cooling with ice, chloromethyl methyl ether (1.04 mL) and potassium carbonate (3.16 g) were added to an acetone (30 mL) solution of 2-bromo-6-nitropyridin-3-ol (1.0 g), and stirred overnight at room temperature. The reaction liquid was concentrated under reduced pressure, ethyl acetate was added to the residue and washed with water and saturated brine. The organic layer was dried with sodium sulfate, then filtered and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient) to give the intended product (1.16 g, 97%) as a brown solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washwashed with water and saturated brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 50%, gradient)

Sources & evidence

ORD record
ord-ed5e930389bc48b1adec12820bd8784c
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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