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

HRID 1666323Notes

Reaction equation

HRID 1666323 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=2)=[N:7][CH:8]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66875457(3-((5-(Trifluoromethyl)pyridin-2-yl)oxy)phenyl)methanol

Product 1

HCID 668758802-(3-(Chloromethyl)phenoxy)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. additionA few minutes into the addition
  2. customa white substance separated
  3. customthis went into solution several minutes
  4. concentrationwas concentrated in vacuo to near dryness (357 g)
  5. addition200 mL of toluene was added to the residue
  6. concentrationthe solution was again concentrated in vacuo
  7. addition200 mL of toluene was added
  8. filtrationsome solid (˜8 g) was filtered off
  9. concentrationThe filtrate was concentrated in vacuo to ˜390 g of dark yellow liquid

Sources & evidence

ORD record
ord-39d8d527111d49078d29870976dee407
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

Loading…