Hydrochloric Acid → 2,3-Dichloro-5-(trichloromethyl)pyridine

HRID 1155471Notes

Reaction equation

HRID 1155471 reaction equation
Br[C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6](C)[CH:7]=1.[ClH:10].ClCl.[C:13]([Cl:17])(Cl)([Cl:15])[Cl:14]>>[Cl:9][C:3]1[C:2]([Cl:10])=[CH:7][C:6]([C:13]([Cl:17])([Cl:15])[Cl:14])=[CH:5][N:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5943Carbon TetrachlorideHCID 24526ChlorineHCID 2854373-Bromo-2-chloro-5-methylpyridine

Product 1

HCID 946472,3-Dichloro-5-(trichloromethyl)pyridine

Procedure

The product from (b) (64 g) in dry carbon tetrachloride (650 ml) was treated with dry hydrogen chloride. The precipitate was broken up and the suspension heated under reflux while dry chlorine was bubbled into the mixture, with illumination from an ultra-violet light source. After 41/2 hours, the mixture was cooled, filtered, and the filtrate evaporated to give the required 2,3-dichloro-5-trichloromethylpyridine. The mass spectrum was consistent with the structure assigned to this compound.

Workup

  1. temperaturethe suspension heated
  2. customwas bubbled into the mixture, with illumination from an ultra-violet light source
  3. temperatureAfter 41/2 hours, the mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-0d3b3796fefe420dbe616ea020020ae6
Source dataset
uspto-grants-1981_11
Patent number
US04302242

Reaction notes

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