HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thionyl Chloride → 3-Chloro-2,4,5-trifluorobenzoyl chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 2,4,5-Trifluorobenzoic acid | HCID 521170 | — |
| Reactant | Potassium Fluoride | HCID 522689 | — |
| Reactant | 3-Chloro-2,4,5-trifluorobenzoic Acid | HCID 2734269 | — |
| Reactant | 3,5-Dichloro-2,4-difluorobenzoyl fluoride | HCID 5463764 | — |
| Reactant | 2,3,4,5-Tetrachlorobenzoyl chloride | HCID 5463797 | — |
| Reactant | 5-Chloro-2,3,4-trifluorobenzoyl fluoride | HCID 13565015 | — |
| Solvent | Sulfolane | HCID 31347 | — |
| Product | 3-Chloro-2,4,5-trifluorobenzoyl chloride | HCID 2782245 | — |
Reaction Steps
The benzoyl halides (1) used as starting materials for this synthetic route are preapred as follows: 3,5-dichloro-2,4-difluorobenzoyl fluoride (boiling point 97°/20 mbar; nD20 =1.5148) and 5-chloro-2,3,4-trifluorobenzoyl fluoride (boiling point 68°-70°/20 mbar; nD20 =1.4764) are obtained together by heating tetrachlorobenzoyl chloride with potassium fluoride in sulpholane at elevated temperatures: ##STR18## The chlorination of 2,4,5-trifluorobenzoic acid in chlorosulphonic acid leads to 3-chloro-2,4,5-trifluorobenzoic acid which is reacted as the crude product with thionyl chloride to give 3-chloro-2,4,5-trifluorobenzoyl chloride (boiling point 94°/18 mbar; nD20 =1.5164): ##STR19##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05072038 |
| Source dataset | uspto-grants-1991_12 |
| ORD ID | ord-2ecf86226bcf43b7963453e550676445 |
| Source note | uspto-grants-1991_12 |