Hydrochloric Acid → 1-Chloroethyl 5-(2,4-difluorophenyl)salicylate

HRID 1719729Notes

Reaction equation

HRID 1719729 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:19]=[C:13]([C:14]([O:16][CH:17]=[CH2:18])=[O:15])[C:12]([OH:20])=[CH:11][CH:10]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:22].Cl>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:19]=[C:13]([C:14]([O:16][CH:17]([Cl:22])[CH3:18])=[O:15])[C:12]([OH:20])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 20266755Vinyl 5-(2,4-difluorophenyl)salicylate

Product 1

HCID 202667581-Chloroethyl 5-(2,4-difluorophenyl)salicylate

Procedure

To a mixture of vinyl 5-(2,4-difluorophenyl)salicylate (15 g) and 0.1 g dry PCl5, HCl gas is passed for about one hour at about 120°-125° C. Upon cooling, the crude product crystallizes and is collected by filtration. Recrystallization from methanol yields pure 1-chloroethyl 5-(2,4-difluorophenyl)salicylate.

Workup

  1. temperatureUpon cooling
  2. customthe crude product crystallizes
  3. filtrationis collected by filtration
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-b93616667151484ebf06b7783337ada1
Source dataset
uspto-grants-1985_09
Patent number
US04542158

Reaction notes

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