Reacción #76361

Ecuación de reacción

bromine

ester

Diethyl 3,4,5-trimethoxyphenylphosphonate

NaHCO3

→

product

Diethyl 2-bromo-3,4,5-trimethoxyphenylphosphonate

Disolventes

acetic acid

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled by an ice water bath
2. 2
   Extracciónextracted with ethyl acetate (3×100 mL)
3. 3
   LavadoThe combined organic phases are washed with 100 mL portions of 5% NaHCO3 until no further gas evolution
4. 4
   LavadoThe organic phases are then washed with brine (100 mL)
5. 5
   Secadodried over anhydrous MgSO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe mixture is purified by flash chromatography

Procedimiento

A solution of bromine (10 mmol) in 10 mL of acetic acid is added dropwise to a solution of ester 11 (10 mmol) in 10 mL of acetic acid cooled by an ice water bath. After the red color of the resulting mixture is discharged, the mixture is poured into saturated NaHCO3 (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic phases are washed with 100 mL portions of 5% NaHCO3 until no further gas evolution is apparent. The organic phases are then washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The mixture is purified by flash chromatography to give the product as a pale yellow solid.

Fuente