Thionyl Chloride → 2,4-Dichloro-5-(chloromethyl)pyridine

HRID 1992649Notes

Reaction equation

HRID 1992649 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9]O.S(Cl)([Cl:13])=O>>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([CH2:9][Cl:13])=[CH:4][N:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2762727(4,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 27627282,4-Dichloro-5-(chloromethyl)pyridine

Procedure

(4,6-Dichloro-pyridin-3-yl)-methanol (2.21 g, 12.41 mmol) is cooled under an atmosphere of argon to 0° C. Thionyl chloride (8 ml) is carefully added. After 5 minutes at 0° C., the solution is heated to reflux. After 10 minutes, TLC analysis indicated complete conversion of the starting material. After cooling to RT, excess thionyl chloride is removed via a membrane pump. The remaining oil is dissolved in EtOAc. The solution is poured into a concentrated aqueous solution of NaHCO3. The organic layer is separated and washed twice with a concentrated aqueous solution of NaCl. After drying over Na2SO4, the organic solvent is removed to afford the title compound of adequate purity for immediate further use. 1H NMR (CDCl3, 400 MHz): δ 4.65 (s, 2H), 7.42 (s, 1H), 8.44 (s,1H). ES+−MS: 195, 197, 199 (3 Cl) [M+H]+.

Workup

  1. temperaturethe solution is heated to reflux
  2. waitAfter 10 minutes
  3. customexcess thionyl chloride is removed via a membrane pump
  4. dissolutionThe remaining oil is dissolved in EtOAc
  5. additionThe solution is poured into a concentrated aqueous solution of NaHCO3
  6. customThe organic layer is separated
  7. washwashed twice with a concentrated aqueous solution of NaCl
  8. dry with materialAfter drying over Na2SO4
  9. customthe organic solvent is removed

Sources & evidence

ORD record
ord-19b86f8a18ae4a2fae8e7e4290c9e5f6
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

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