Reacción #45623

Ecuación de reacción

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

water

N-bromosuccinimide

→

compound

Rendimiento 81.2%

6-(2-Bromoacetyl)-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 81.2%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter the reaction
2. 2
   Otrothe solvent was evaporated away under reduced pressure
3. 3
   Lavadoby washing with water and saturated brine
4. 4
   SecadoThe obtained organic layer was dried over anhydrous sodium sulfate
5. 5
   Otrothe solvent was evaporated away under reduced pressure
6. 6
   Lavadoeluted with a mixed solvent of n-hexane/ethyl acetate (2:1

Procedimiento

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile (I-84) (2.58 g, 8.46 mmol) was dissolved in tetrahydrofuran (130 ml), water (7.7 ml) and N-bromosuccinimide (1.61 g, 8.89 mmol) were added all at a time, followed by stirring at room temperature for 1.5 hours. After the reaction, the solvent was evaporated away under reduced pressure, followed by dilution with ethyl acetate and by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography (covering) and eluted with a mixed solvent of n-hexane/ethyl acetate (2:1, v/v) to obtain the entitled compound (2.40 g, 81%) as a yellow white solid.

Fuente