Thionyl Chloride → 2-(3-(Chloromethyl)phenoxy)-5-(trifluoromethyl)pyridine

Participants

Reaction Steps

To a solution of [3-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-methanol (281.0 g, 1.044 moles) in dichloromethane (2.0 L) at −5° C. was added dropwise over a 25 min period thionyl chloride (136.6 g, 1.148 mol). A few minutes into the addition, a white substance separated but this went into solution several minutes later. The reaction was stirred at ambient temperature for 1 h and then was concentrated in vacuo to near dryness (357 g). 200 mL of toluene was added to the residue and the solution was again concentrated in vacuo to near dryness. 200 mL of toluene was added and some solid (˜8 g) was filtered off. The filtrate was concentrated in vacuo to ˜390 g of dark yellow liquid.

Provenance & Evidence