Reacción #2446096

Ecuación de reacción

Potassium hydroxide

THF

dibenzofuran-4-boronic acid

Triphenylphosphine

→

4-Vinyl-dibenzofuran

Rendimiento 42.0%

Disolventes

H2O

Ethylacetate

Dichloromethane

Methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a magnetic stirrer and a reflux condenser
2. 2
   TemperaturaThe mixture is refluxed
3. 3
   TemperaturaThe reaction mixture is heated to 60° C. internal temperature
4. 4
   Temperaturacooled down to room temperature
5. 5
   ExtracciónThe organic phase is extracted twice with water and once with brine
6. 6
   SecadoThe organic phase is dried over Sodiumsulfate
7. 7
   Otrothe solvent evaporated
8. 8
   OtroThe crude product is purified by column chromatography (Heptane)

Procedimiento

16.09 g (0.259 mol) of Potassium hydroxide (86%) are placed in a 500 ml three necked round bottomed flask equipped with a magnetic stirrer and a reflux condenser. 200 ml of THF and 6.5 ml of Dichloromethane are added. The mixture is refluxed. After 1 hour the mixture is cooled to room temperature. A solution of 8 g (37.74 mmol) dibenzofuran-4-boronic acid, 0.8 g (3.02 mmol) of Triphenylphosphine, 339 mg (0.7 mmol) of Palladium (II) acetate and 200 ml of Methanol are added. The reaction mixture is heated to 60° C. internal temperature. After 2 hours the reaction is complete and cooled down to room temperature. The mixture is diluted with H2O and Ethylacetate. The organic phase is extracted twice with water and once with brine. The organic phase is dried over Sodiumsulfate and the solvent evaporated. The crude product is purified by column chromatography (Heptane). 4-Vinyl-dibenzofuran is isolated in 42% yield.

Fuente