Thionyl Chloride → 2-Chloro-5-(chloromethyl)-3-methoxypyridine

HRID 2234222Notes

Reaction equation

HRID 2234222 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[O:10][CH3:11].S(Cl)([Cl:14])=O>ClCCl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][C:5]([CH2:8][Cl:14])=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59297074(6-Chloro-5-methoxypyridin-3-yl)methanol

Product 1

HCID 592970732-Chloro-5-(chloromethyl)-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-chloro-5-methoxypyridin-3-yl)methanol (0.50 g, 2.9 mmol) in dichloromethane (14 mL) at 25° C. was added thionyl chloride (230 μL, 3.2 mmol) dropwise. Let stir for 5 h, then the reaction was quenched with saturated aqueous NaHCO3 and extracted with dichloromethane (3×). The combined organic layer were dried over MgSO4 and concentrated to furnish the product 2-chloro-5-chloromethyl-3-methoxypyridine that was 96% pure by GC-MS. The product was used immediately in the next step without further purification. GC-MS: Exact mass calcd for C7H7Cl2NO [M]+, 191. Found 191.

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-188665bf791d4779bc8545ca2bd1f113
Source dataset
uspto-grants-2010_05
Patent number
US07709649B2

Reaction notes

Loading…