Water → 2-Chloro-4-(chloromethyl)pyridine
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- customThe phases are separated
- washthe organic phase is washed with water
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-92422a956bf04cd28d557a55a375e905
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935819B2
Reaction notes
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