Thionyl Chloride → (3,5-Dichloro-6-fluoro-2-pyridyloxy)acetyl chloride

HRID 1448412Notes

Reaction equation

HRID 1448412 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([OH:14])=O)=[N:4][C:5]([F:9])=[C:6]([Cl:8])[CH:7]=1.S(Cl)([Cl:17])=O>>[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([Cl:17])=[O:14])=[N:4][C:5]([F:9])=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20379575(3,5-Dichloro-6-fluoro-2-pyridyloxy) acetic acid

Product 1

HCID 20379628(3,5-Dichloro-6-fluoro-2-pyridyloxy)acetyl chloride

Procedure

A solution was prepared by admixing 8.6 grams (0.036 mole) of 3,5-dichloro-6-fluoro-2-pyridyloxy acetic acid in 15 milliliters of thionyl chloride. The mixture was refluxed for about 50 minutes. At the completion of the reaction, the excess thionyl chloride was removed by distillation. The liquid residue was cooled and the crystals which formed were separated. The (3,5-dichloro-6-fluoro-2-pyridyloxy)acetyl chloride product was recovered in a yield of 8.4 grams (92 percent of theoretical). Upon analysis, the product was found to have carbon, hydrogen, chlorine and nitrogen contents of 32.9, 0.9, 41.9 and 5.3 percent, respectively as compared with the theoretical contents of 32.8, 0.4, 41.4 and 5.5 percent, respectively, as calculated for the above-named compound.

Workup

  1. customA solution was prepared
  2. temperatureThe mixture was refluxed for about 50 minutes
  3. customAt the completion of the reaction
  4. customthe excess thionyl chloride was removed by distillation
  5. temperatureThe liquid residue was cooled
  6. customthe crystals which formed
  7. customwere separated
  8. customThe (3,5-dichloro-6-fluoro-2-pyridyloxy)acetyl chloride product was recovered in a yield of 8.4 grams (92 percent of theoretical)

Sources & evidence

ORD record
ord-85ed653cad734f2d98f19c449b25a007
Source dataset
uspto-grants-1979_12
Patent number
US04180395

Reaction notes

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