Thionyl Chloride → 2-Chloro-4-(chloromethyl)pyridine

HRID 1257102Notes

Reaction equation

HRID 1257102 reaction equation
O=S(Cl)[Cl:3].[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][N:7]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12][Cl:3])[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7062237(2-Chloropyridin-4-yl)methanol

Product 1

HCID 111265732-Chloro-4-(chloromethyl)pyridineYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

SOCl2 (4.2 g, 35.5 mol) was added dropwise to a suspension of the alcohol (5 g, 34.8 mmol) in CH2Cl2 (50 mL) at −5° C. with stirring. The mixture was stirred at room temperature overnight, then quenched with water (100 mL), and extracted with CH2Cl2 (3×100 mL). The organic layers were combined, washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated to dryness. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/5) and afforded the title compound (5.5 g, near quantitative yield) as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customquenched with water (100 mL)
  3. extractionextracted with CH2Cl2 (3×100 mL)
  4. washwashed with brine (200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/5)

Sources & evidence

ORD record
ord-2bda278594014d9aa6155af455fdb07b
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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