Reacción #4769

Ecuación de reacción

potassium carbonate

phosphorus tribromide

tetrahydrofuran

5-hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

tetrahydrofuran

→

5-bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder cooling at 7°-10° C
2. 2
   Extracciónextracted with ethyl acetate (300 ml)
3. 3
   FiltraciónAfter filtering off an insolble material
4. 4
   Lavadothe organic layer was washed with saturated aqueous sodium chloride
5. 5
   Secadodried over magnesium sulfate
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe residue was recrystallized from diethyl ether

Procedimiento

To a solution of phosphorus tribromide (16.85 g) in a mixture of benzene (150 ml) and tetrahydrofuran (150 ml) was dropwise added a solution of 5-hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g) in tetrahydrofuran (150 ml) under cooling at 7°-10° C. After stirring for 4 hours at the same temperature, the reaction mixture was poured into ice-water (200 ml), adjusted to pH 9.5 with saturated potassium carbonate and extracted with ethyl acetate (300 ml). After filtering off an insolble material, the organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from diethyl ether to give 5-bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (29.08 g).

Fuente