Reacción #172485

Ecuación de reacción

3,5-dimethoxybromobenzene

dibutylamine

potassium bistrimethylsilylamide

→

4-dibutylamino-3,5-dimethoxybenzene

Rendimiento 88.2%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGAfter well-stirred
3. 3
   Temperaturathe mixture was heated
4. 4
   Temperaturaunder reflux
5. 5
   workup.STIRRINGwith stirring overnight
6. 6
   Extracciónsubjected to 3 times of extraction with 200 ml of chloroform
7. 7
   LavadoWashing with a saturated saline solution
8. 8
   Secadodrying over anhydrous magnesium sulfate, and concentration
9. 9
   OtroThe residue was purified by silica gel chromatography

Procedimiento

In a stream of argon, to 300 ml of dioxane were added 21.7 g (100 mmol) of 3,5-dimethoxybromobenzene and 13.0 g (100 mmol) of dibutylamine, and 22.0 g (110 mmol) of potassium bistrimethylsilylamide was added thereto with stirring. After well-stirred, the mixture was heated under reflux with stirring overnight. The reactant was poured into 2 L of ice water and subjected to 3 times of extraction with 200 ml of chloroform. Washing with a saturated saline solution, drying over anhydrous magnesium sulfate, and concentration were performed. The residue was purified by silica gel chromatography to give 23.4 g (yield: 88%) of 4-dibutylamino-3,5-dimethoxybenzene as a colorless transparent oily matter.

Fuente