Reaction #2446096

Reaction equation

Potassium hydroxide

THF

dibenzofuran-4-boronic acid

Triphenylphosphine

→

4-Vinyl-dibenzofuran

Yield 42.0%

Solvents

H2O

Ethylacetate

Dichloromethane

Methanol

Conditions

Workup

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

Procedure

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