Reacción #45552

Ecuación de reacción

water

dichloromethane

N-(3-bromo-6-cyano-2-methoxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide

dichloromethane

tribromoborane

→

compound

Rendimiento 97.3%

N-(3-Bromo-6-cyano-2-hydroxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide

Rendimiento 97.3%

Disolventes

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfterwards, this was heated up to −12° C.
2. 2
   workup.STIRRINGstirred for 1 hour
3. 3
   OtroThe reaction liquid
4. 4
   workup.ADDITIONwas added
5. 5
   Extracciónthe intended product was extracted with ethyl acetate (50 ml×2)
6. 6
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure

Procedimiento

A dichloromethane (1.0 ml) solution of N-(3-bromo-6-cyano-2-methoxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide (I-11) (34 mg, 79.6 μmol) was cooled at −78° C., a dichloromethane solution of 1 N tribromoborane (239 μl, 239 μmol) was dropwise added, followed by stirring at −78° C. for 70 minutes. Afterwards, this was heated up to −12° C. and stirred for 1 hour. The reaction liquid was put into cold water (50 ml), saturated brine (50 ml) was added, the intended product was extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure to obtain the entitled compound (32 mg, 96%) as a yellow white semi-solid.

Fuente