Thionyl Chloride → 2-(Chloromethyl)-6-methoxypyridine

HRID 78088Notes

Reaction equation

HRID 78088 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:13])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:13][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 12325389(6-Methoxypyridin-2-yl)methanol

Product 1

HCID 178542282-(Chloromethyl)-6-methoxypyridineYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of dichloromethane (5 mL) and the (6-methoxy-pyridin-2-yl)-methanol (105 mg, 0.75 mmol) described in Manufacturing Example 99-1-1 was added thionyl chloride (82.4 μL, 1.13 mmol), which was stirred for 30 minutes at room temperature. A saturated sodium hydrogencarbonate aqueous solution was added to this reaction mixture, which was then extracted with dichloromethane. 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 to obtain the title compound (105.8 mg, 89%).

Workup

  1. extractionwas then extracted with dichloromethane
  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

Sources & evidence

ORD record
ord-4665b866665549e2b597ee0f2f1e711c
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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