HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 5-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one | HCID 2758231 | — |
| Reactant | 3'-Cyano-4'-fluoroacetophenone | HCID 22458389 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 5-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-fluorobenzonitrile | HCID 86642189 | 46% |
Reaction Steps
163 mg of 1-(3,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone (VIa) (Journal of Physical Organic Chemistry (1989), 2(4), 363-6), 486 mg of 5-acetyl-2-fluoro-benzonitrile (CAS:288309-07-9) and 276 mg of potassium carbonate in 5 ml of dry toluene were refluxed for 72 hours. The solvent was then evaporated under reduced pressure and the residue was purified on silica gel (eluent hexane/ethyl acetate 6:1) affording 5-[3-(3,5-Dichloro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-2-fluoro-benzonitrile as a yellow resin in 46% yield (solidified on standing). 1H-NMR (CDCl3, δ in ppm): 8.05-8.11 (m, 2H), 7.33-7.43 (m, 3H), 7.15 (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08754053B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-90326a1cc41442708b215db59f93bddc |
| Source note | uspto-grants-2014_06 |