Thionyl Chloride → 2-Chloro-6-(chloromethyl)pyridine

HRID 77924

Reaktionsgleichung

Reaktionsgleichung von HRID 77924
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][Cl:12])[N:7]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 182139(6-Chloropyridin-2-yl)methanolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 155744402-Chloro-6-(chloromethyl)pyridineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of (6-chloro-pyridine-2-yl)-methanol (200 mg, 1.39 mmol) described in Manufacturing Example 52-1-1 and toluene (3 mL) was added thionyl chloride (152 μL, 2.09 mmol) on an ice bath, which was stirred for 2 hours at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (163.2 mg, 73%).

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-89810865de7445d9990ea6926ef5c889
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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