Thionyl Chloride → 2-Chloro-5-(chloromethyl)pyridine

HRID 1087093Notes

Reaction equation

HRID 1087093 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][N:3]=1.S(Cl)([Cl:12])=O>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Cl:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridineYield 95.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of 70.3g of 2-chloro-5-(hydroxymethyl) pyridine and 50ml of 1,2-dichloroethane was dropwise added to a mixture of 87.4g of thionyl chloride and 100ml of 1,2-dichloroethane during 30 minutes in a water bath of 5-20° C. The mixture was stirred for an hour and a half at room temperature and for 4 hours and a half under refluxing. After concentrating, to the residue were added 200ml of chloroform and 60ml of water and then added portionwise 20g of sodium hydrogen carbonate under stirring. The organic phase was separated, treated with active carbon and concentrated to obtain 75.9g of 2-chloro-5-(chloromethyl)pyridine as a yellowish brown solid.

Workup

  1. temperaturea half under refluxing
  2. concentrationAfter concentrating, to the residue
  3. additionwere added 200ml of chloroform and 60ml of water
  4. additionadded portionwise 20g of sodium hydrogen carbonate
  5. stirringunder stirring
  6. customThe organic phase was separated
  7. additiontreated with active carbon
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d372869b2e9e49469bd26e202af3548a
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Reaction notes

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