Réaction #84865

Équation de réaction

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

formamide

EtOAc

NaHCO3

→

4-(4-bromo-3,5-dimethoxyphenyl)-5-methyloxazole

Rendement 55.0%

Conditions de réaction

Traitement

1. 1
   ExtractionIt was then extracted with EtOAc twice
2. 2
   Lavagethe combined organics were washed with H2O and brine
3. 3
   Séchagedried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   AutrePurification by chromatography (30% EtOAc-hexanes)

Mode opératoire

A solution of 2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one (1.07 g, 3.04 mmol) in formamide (10 mL) in an oven-dried flask under argon was heated at 110° C. for 16 hrs. After cooling to room temp, EtOAc and saturated aqueous NaHCO3 were carefully added and the mixture was stirred for 15 minutes. It was then extracted with EtOAc twice and the combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated. Purification by chromatography (30% EtOAc-hexanes) gave 4-(4-bromo-3,5-dimethoxyphenyl)-5-methyloxazole as a yellow solid (0.496 g, 55% yield).

Source