Thionyl Chloride → 4-(Chloromethyl)-2-methoxypyridine

HRID 2252841Notes

Reaction equation

HRID 2252841 reaction equation
O=S(Cl)[Cl:3].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][N:8]=1>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH2:13][Cl:3])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14462410(2-Methoxypyridin-4-yl)methanol

Product 1

HCID 179484394-(Chloromethyl)-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.57 ml (21.6 mmol) of SOCl2 are added dropwise, whilst cooling with ice and under a N2 atmosphere, to a solution of 1.5 g (10.8 mmol) of 2-methoxy-4-(hydroxymethyl)-pyridine [for preparation see J. Org. Chem. 54 (1989), 5580] in 13 ml of chloroform. After 16 h at RT, the mixture is concentrated by evaporation, water and 2N sodium hydroxide solution are added to the residue, and extraction immediately takes place 3 times with chloroform. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated by evaporation to form 2-methoxy-pyridin-4-yl-methylchloride; 1H NMR (CDCl3) δ 8.15 (d, 1H), 6.90 (d, 1H), 6.76 (s, 1H), 4.49 (s, 2H), 3.94 (s, H3C).

Workup

  1. concentrationthe mixture is concentrated by evaporation, water and 2N sodium hydroxide solution
  2. additionare added to the residue, and extraction immediately takes place 3 times with chloroform
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-578fa8c941704b0694a721961e88ed25
Source dataset
uspto-grants-2008_01
Patent number
US07323474B2

Reaction notes

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