Réaction #417945

Équation de réaction

5-bromo-2-ethoxy-pyridine

urea hydrogen peroxide

→

3-Bromo-6-ethoxy-2-methoxy-pyridine

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONare added
2. 2
   TempératureAfterwards cooling
3. 3
   Autreis removed
4. 4
   AutreThe solvent is removed in vacuo, water
5. 5
   workup.ADDITIONis added
6. 6
   Extractionthe resulting mixture is extracted with DCM
7. 7
   Séchagelayers are dried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Autrethe sovent is removed in vacuo
10. 10
    AutreThe crude product is purified by column chromatography (silica gel, DCM/MeOH)

Mode opératoire

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).

Source