Réaction #2446096

Équation de réaction

Potassium hydroxide

THF

dibenzofuran-4-boronic acid

Triphenylphosphine

→

4-Vinyl-dibenzofuran

Rendement 42.0%

Solvants

H2O

Ethylacetate

Dichloromethane

Methanol

Conditions de réaction

Traitement

1. 1
   Autreequipped with a magnetic stirrer and a reflux condenser
2. 2
   TempératureThe mixture is refluxed
3. 3
   TempératureThe reaction mixture is heated to 60° C. internal temperature
4. 4
   Températurecooled down to room temperature
5. 5
   ExtractionThe organic phase is extracted twice with water and once with brine
6. 6
   SéchageThe organic phase is dried over Sodiumsulfate
7. 7
   Autrethe solvent evaporated
8. 8
   AutreThe crude product is purified by column chromatography (Heptane)

Mode opératoire

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.

Source