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

HRID 1691031Notes

Reaction equation

HRID 1691031 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-c4be256d971349ce8ac606e3c1485982
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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