3-Cyanopyridine → 2-(3-Bromophenyl)oxirane

HRID 1825048

Reaktionsgleichung

Reaktionsgleichung von HRID 1825048
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH2:9])[CH:3]=1.C(C1C=NC=CC=1)#N.OO.S([O-])([O-])=[O:21].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C[Re](=O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][O:21]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 5

HCID 793-CyanopyridineHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 748703-BromostyreneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 1471932-(3-Bromophenyl)oxirane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178477782HCID 178477782, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Bromo-3-vinyl-benzene (5 g, 27.3 mmol) and 3-cyanopyridine (551 mg, 2.7 mmol) were added in CH2Cl2 (25 mL), Methyltrioxorhenium (VII) (34 mg, 0.137 mmol) and hydrogen peroxide (30%) (6.2 mL, 54.6 mmol) were added and the reaction mixture was stirred at room temperaute for 18 h. Sodium sulfite 1M (10 mL) and saturated sodium bicarbonate were added, the aqueous layer was extracted with CH2Cl2, and the combined organic layers were dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated in vacuo to provide the title compound as clear oil ((5.05 g, 93%).

Aufarbeitung

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4acb0c56d7ad4b6ca7f8c325a5b3bae3
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045551B2

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