Réaction #84864

Équation de réaction

NaHCO3

1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one

pyridinium tribromide

→

2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one

Rendement 56.4%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   ExtractionThe mixture was extracted with EtOAc the combined
2. 2
   Lavageorganics were washed with saturated aqueous NaHCO3 and brine
3. 3
   Séchagethen dried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutrePurification by chromatography (10-20% EtOAc-hexanes)

Mode opératoire

To a solution of 1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one (1.50 g, 5.49 mmol) in anhydrous THF (20 mL) was added pyridinium tribromide (1.93 g, 6.04 mmole). The reaction was stirred at room temperature for 2 hrs then neutralized with a solution of saturated aqueous NaHCO3. The mixture was extracted with EtOAc the combined organics were washed with saturated aqueous NaHCO3 and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (10-20% EtOAc-hexanes) gave 2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one as an orange oil (1.09 g, 56% yield).

Source