Thionyl Chloride → 3-Chloro-5-(chloromethyl)-2-pyridinecarbonitrile

HRID 340268Notes

Reaction equation

HRID 340268 reaction equation
[Cl:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([CH2:8]O)[CH:7]=1.S(Cl)([Cl:14])=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][CH:5]=[C:6]([CH2:8][Cl:14])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58001719HCID 58001719, compound

Product 1

HCID 668753003-Chloro-5-(chloromethyl)-2-pyridinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-chloro-5-(hydroxymethyl)picolinonitrile (from the previous step) in CH2Cl2 (0.2 M) at 0° C. was added thionyl chloride (10 eq). After stirring at room temperature overnight the reaction mixture was concentrated under vacuum and the resulting crude was purified by chromatography (silica gel, 20-50% EtOAc in hexanes) to afford 3-chloro-5-(chloromethyl)picolinonitrile as a colorless oil.

Workup

  1. concentrationwas concentrated under vacuum
  2. customthe resulting crude was purified by chromatography (silica gel, 20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8058ff92a6064d7b8de1eded267a20c8
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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