Thionyl Chloride → 2-(Chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridine

HRID 715391Notes

Reaction equation

HRID 715391 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[N:10]=[C:9]([CH2:11]O)[CH:8]=[CH:7][CH:6]=1.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:17][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:3][C:2]([F:14])([F:13])[F:1])[N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 62240732(6-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanol

Product 1

HCID 622388462-(Chloromethyl)-6-(2,2,2-trifluoroethoxy)pyridineYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-(2,2,2-trifluoroethoxy)pyridin-2-yl)methanol (0.32 g, 1.55 mmol, Step-3), and thionyl chloride (0.23 mL, 3.10 mmol) in DCM (16 mL) is stirred at rt for 1 hour. The organic solvent is concentrated under reduced pressure and dried to give 0.35 g (>99% yield) of the title compound as yellow oil. This material is used for the next reaction (Step-5) without further purification.

Workup

  1. concentrationThe organic solvent is concentrated under reduced pressure
  2. customdried

Sources & evidence

ORD record
ord-42240215459f465aab73064358618287
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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