Azobisisobutyronitrile → 2-(Bromomethyl)-6-chloro-4-(trifluoromethyl)pyridine

HRID 656507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656507
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=[C:2]([Cl:1])[N:3]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27366262-Chloro-6-methyl-4-(trifluoromethyl)pyridine

Produkt 1

HCID 534037392-(Bromomethyl)-6-chloro-4-(trifluoromethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(2-chloro-6-methyl-4-(trifluoromethyl)pyridine (10.0 g, 51 mmol), N-bromosuccinimide (10.9 g, 61 mmol), and 2,2′-azobis(2-methylpropionitrile) (164 mg, 1 mmol) were combined in carbon tetrachloride (200 mL) and heated to reflux. After 16 h, the reaction mixture was cooled to 0° C. and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (100% hexanes) to produce 9.1 g (70%) as a light yellow oil. 1H-NMR (CDCl3, 400 MHz) δ 7.59 (s, 1H), 7.47 (s, 1H), 4.52 (s, 2H).

Aufarbeitung

  1. temperatureheated to reflux
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography on silica gel (100% hexanes)
  5. customto produce 9.1 g (70%) as a light yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-d91be12602ff4ae586b7113958d65e12
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071778B2

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