Carbamide Peroxide → 3-Bromo-6-ethoxy-2-methoxypyridine

HRID 330763Notes

Reaction equation

HRID 330763 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.OO.N[C:14](N)=[O:15]>C(Cl)Cl>[Br:1][C:2]1[C:7]([O:15][CH3:14])=[N:6][C:5]([O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31294Carbamide PeroxideHCID 8172375-Bromo-2-ethoxypyridine

Product 1

HCID 903020483-Bromo-6-ethoxy-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5.00 g (24.7 mmol) 5-bromo-2-ethoxy-pyridine in 50 mL DCM are added 4.66 g (49.5 mmol) urea hydrogen peroxide. Then the mixture is chilled to 0° C. before 6.88 mL (49.5 mmol) TFA anhydride are added. Afterwards cooling is removed and the resulting mixture is stirred over night while the temperature raises to r.t. The solvent is removed in vacuo, water is added and the resulting mixture is extracted with DCM. The combined org. layers are dried over MgSO4, filtered and the sovent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH).

Workup

  1. additionare added
  2. temperatureAfterwards cooling
  3. customis removed
  4. customThe solvent is removed in vacuo, water
  5. additionis added
  6. extractionthe resulting mixture is extracted with DCM
  7. dry with materiallayers are dried over MgSO4
  8. filtrationfiltered
  9. customthe sovent is removed in vacuo
  10. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH)

Sources & evidence

ORD record
ord-ca4c1f1787f5427985a3234ebe7520ed
Source dataset
uspto-grants-2014_11
Patent number
US08877741B2

Reaction notes

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