Water → 2-Chloro-4-(chloromethyl)pyridine

HRID 546567

Reaction equation

HRID 546567 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:12])=O.CN(C)C=O.O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:12])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 111265732-Chloro-4-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11.3 g of 2-chloro-4-hydroxymethylpyridine obtained in stage a) below in 200 mL of dichloromethane are added dropwise 6.896 mL of thionyl chloride, followed by 2.1 mL of dimethylformamide, the reaction mixture is stirred for 3 hours at room temperature and 50 mL of water are then added dropwise. The phases are separated and the organic phase is washed with water, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 12.8 g of 2-chloro-4-chloromethylpyridine in the form of an amber-coloured liquid, which is used without further purification.

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92422a956bf04cd28d557a55a375e905
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Linked notes

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