Thionyl Chloride → 2,3-Bis(chloromethyl)pyridine

HRID 722143Notes

Reaction equation

HRID 722143 reaction equation
[ClH:1].O[CH2:3][C:4]1[C:9]([CH2:10]O)=[CH:8][CH:7]=[CH:6][N:5]=1.S(Cl)([Cl:14])=O>>[Cl:1][CH2:3][C:4]1[C:9]([CH2:10][Cl:14])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 17750570(Pyridine-2,3-diyl)dimethanol--hydrogen chloride (1/1)

Product 1

HCID 145187502,3-Bis(chloromethyl)pyridine

Procedure

2,3-bis(hydroxymethyl)pyridine hydrochloride (JP 49 020181) (2.7 g, 15.4 mmol) was added portionwise to stirred thionyl chloride (20 mL) at 0° C. under nitrogen. The cooling bath was removed, and the reaction allowed to come to room temperature, then heated at reflux for one hour. The dark mixture was allowed to cool to room temperature, then the thionyl chloride was removed in vacuo. The residue was azeotroped with toluene (x2), the brown solid residue treated with ice, basified with Na2CO3 (sat), then extracted with diethyl ether (x3). The combined extracts were dried (Na2SO4), filtered and evaporated to give 2,3-bis(chloromethyl)pyridine (2.6 g) as a red/brown liquid. This material was used immediately in the next step.

Workup

  1. customThe cooling bath was removed
  2. customto come to room temperature
  3. temperatureheated
  4. temperatureat reflux for one hour
  5. customthe thionyl chloride was removed in vacuo
  6. customThe residue was azeotroped with toluene (x2)
  7. additionthe brown solid residue treated with ice
  8. extractionextracted with diethyl ether (x3)
  9. dry with materialThe combined extracts were dried (Na2SO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-e7f22a92cc81405d9282ee06d0b5a03c
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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