Thionyl Chloride → 2-(Chloromethyl)-6-(trifluoromethyl)pyridine

HRID 17014Notes

Reaction equation

HRID 17014 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:15])=O>C(Cl)Cl>[Cl:15][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:12])([F:11])[F:1])[N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14761464[6-(Trifluoromethyl)pyridin-2-yl]methanol

Product 1

HCID 673570732-(Chloromethyl)-6-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Trifluoromethylpyridin-2-yl)methanol (760 mg, 4.3 mmol) was dissolved in CH2Cl2 and thionyl chloride was added slowly at room temperature. The reaction mixture was stirred at room temperature for 4 h. Solvent was removed under the reduced pressure, the pH was adjusted to 5, and the product was extracted with EtOAc. Purification by flash column (5% EtOAc-Hexane) gave 2-chloromethyl-6-trifluoromethylpyridine (200 mg) as a white solid.

Workup

  1. customSolvent was removed under the reduced pressure
  2. extractionthe product was extracted with EtOAc
  3. customPurification by flash column (5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-cc469430f8e64d66bc06923fb2ae540e
Source dataset
uspto-grants-2010_06
Patent number
US07737300B2

Reaction notes

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