Reaction #710496

Reaction equation

[4-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol

SOCl2

→

4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine

Yield 87.0%

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for 1 hour
2. 2
   ConcentrationThe mixture was concentrated
3. 3
   workup.ADDITIONthe residue was poured into water (1 L)
4. 4
   ExtractionThe mixture was extracted with ethyl acetate (500 mL*3)
5. 5
   ConcentrationThe combined organic layer was concentrated

Procedure

[4-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-12) (90 g, 0.426 mol) was added to SOCl2 (700 mL) slowly with ice bath, the mixture was refluxed for 1 hour. The mixture was concentrated and the residue was poured into water (1 L). The mixture was adjusted to pH=7-8 with solid NaHCO3. The mixture was extracted with ethyl acetate (500 mL*3). The combined organic layer was concentrated to yield 4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine (Int-13) (80 g, 87%) as brown syrup which was used for the next step without further purification.

Source