반응 #2446096

ord-204c9193d92d4364a927c2c4dc7ca029

반응 방정식

[K+].[OH-]
Potassium hydroxide
C1CCOC1
THF
OB(O)c1cccc2c1oc1ccccc12
dibenzofuran-4-boronic acid
c1ccc(P(c2ccccc2)c2ccccc2)cc1
Triphenylphosphine
C=Cc1cccc2c1oc1ccccc12
4-Vinyl-dibenzofuran
수율 42.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타equipped with a magnetic stirrer and a reflux condenser
  2. 2
    온도The mixture is refluxed
  3. 3
    온도The reaction mixture is heated to 60° C. internal temperature
  4. 4
    온도cooled down to room temperature
  5. 5
    추출The organic phase is extracted twice with water and once with brine
  6. 6
    건조The organic phase is dried over Sodiumsulfate
  7. 7
    기타the solvent evaporated
  8. 8
    기타The crude product is purified by column chromatography (Heptane)

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08685541B2uspto-grants-2014_04