Water → 3-Chloro-5-(trifluoromethyl)pyridine

HRID 606786

Reaktionsgleichung

Reaktionsgleichung von HRID 606786
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.O.N1C=CC=CC=1CC=O>[Zn].C(O)(=O)C>[Cl:8][C:7]1[CH:2]=[N:3][CH:4]=[C:5]([C:9]([F:11])([F:10])[F:12])[CH:6]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 117151722-(Pyridin-2-YL)acetaldehyde

Produkt 1

HCID 27366983-Chloro-5-(trifluoromethyl)pyridineAusbeute 7,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Add zinc dust (1.18 g) to a suspension of 2,3-dichloro-5-trifluoromethyl-pyridine (2.0 g, 9.30 mmol) in 80:20 water and acetic acid (5 mL) and stir at 90° C. for 1 h. Add more zinc dust (1g) and stir at 90° C. for an additional 15 min. Cool the reaction mixture to room temperature, filter, and wash with dichloromethane. Carefully concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 0:100 hexane:dichloromethane, to obtain the title compound as a volatile oil (0.120g, 7%).

Aufarbeitung

  1. stirringstir at 90° C. for an additional 15 min
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter
  4. washwash with dichloromethane
  5. concentrationCarefully concentrate
  6. custompurify the residue by silica gel chromatography
  7. washeluting with 100:0 to 0:100 hexane

Quellen und Nachweise

ORD-Eintrag
ord-a90e4a127c254a10a0cebcff8276d27e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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