Triphenylphosphine → HCID 123876700, Verbindung

HRID 712674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712674
[CH3:1][S:2]([CH2:5][CH:6]=[CH2:7])(=[O:4])=[O:3].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13](Br)[CH:14]=1.CC([O-])=O.[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:7]=[CH:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:14]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 693693,5-DibromopyridineHCID 1400483-Methanesulfonylprop-1-eneHCID 517045Sodium Acetate

Produkt 1

HCID 123876700HCID 123876700, VerbindungAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-Methanesulfonyl-propene (2.4 g, 20 mmol), 3,5-dibromo-pyridine (4.7 g, 20 mmol), NaOAc (1.9 g, 60 mmol), PPh3 (1.6 g, 6.0 mmol) and Pd(OAc)2 (450 mg, 2.0 mmol) are mixed in 1,4-dioxane (350 ml) and heated to reflux for 16 hrs. The reaction mixture is filtered and the filtrate is concentrated. The residue is taken up in DCM and washed with water. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by flash column chromatography to give 2.0 g of 3-bromo-5-(-3-methanesulfonyl-propenyl)-pyridine with some PPh3O.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 16 hrs
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. washwashed with water
  6. dry with materialThe organic layer is dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-833c474a4a0a4adb9b3f78dfc73dae3c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181272B2

Notizen zur Reaktion

Wird geladen…