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

HRID 2224337Notes

Reaction equation

HRID 2224337 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9]O.O=S(Cl)[Cl:13]>C(Cl)Cl>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([CH2:9][Cl:13])=[CH:4][N:5]=1

Participants

4

Reactant 2

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

Product 1

HCID 27627282,4-Dichloro-5-(chloromethyl)pyridineYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 41A (2.5 g, 14 mmol) in CH2Cl2 (20 mL) was added slowly SOCl2 (1.2 mL, 14 mmol) at room temperature. The reaction was stirred for 15 minutes, cooled to 0° C. and washed with saturated aqueous NaHCO3. The CH2Cl2 layer was dried (MgSO4), concentrated in vacuo and purified by flash chromatography (SiO2, CH2Cl2) to give 41B (1.3 g, 47%).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe CH2Cl2 layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-bd18a2db729e4e7c8caf200efec7aa05
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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