Water → 2-Chloro-5-(chloromethyl)pyridine

HRID 377017Notes

Reaction equation

HRID 377017 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5](CO)=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:11].[CH:16]([Cl:19])(Cl)Cl.O>P(Cl)(Cl)(Cl)=O>[Cl:11][C:2]1[CH:7]=[CH:6][C:5]([CH2:16][Cl:19])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 24819Phosphorus pentachlorideHCID 178519722HCID 178519722, compound

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 2.5 g (20 mmol) of 2-hydroxy-5-hydroxymethylpyridine and 4.16 g of phosphorus pentachloride in 10 ml of phosphoryl chloride was stirred for 6 hours at 105° C. After cooling, 50 ml of chloroform was added, the excess chlorination reagent being hydrolyzed by careful addition of water. The organic phase was washed with NaHCO3 solution, dried on NaSO4 and concentrated by evaporation. The distillation of the oily residue at 16 mm and 120° C. yielded 3.08 g of 2-chloro-5-chloromethyl-pyridine as a colorless oil that solidified during the cooling. The latter corresponds to a yield of 95 percent relative to the 2-hydroxy-5-hydroxymethyl-pyridine. Further data concerning the product was:

Workup

  1. temperatureAfter cooling
  2. washThe organic phase was washed with NaHCO3 solution
  3. customdried on NaSO4
  4. concentrationconcentrated by evaporation
  5. distillationThe distillation of the oily residue at 16 mm and 120° C.

Sources & evidence

ORD record
ord-cbe586667a974709bb9c1ee8114e5327
Source dataset
uspto-grants-2000_02
Patent number
US06022974

Reaction notes

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