HuagongsheHuagongshe Chemistry Print Report · For research reference only
Thiophosgene → 5-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Thiophosgene | HCID 10040 | — |
| Reactant | 4-Amino-5-fluoro-2-(trifluoromethyl)benzonitrile | HCID 68292928 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile | HCID 86711810 | 88% |
Reaction Steps
To a solution of the compound 25 (660 mg, 3.25 mmol) in THF (6 mL) was added a solution of thiophosgene (1 mL, 13 mmol) in water (1 mL) slowly at room temperature. The reaction mixture was stirred for 1 h, then concentrated in vacuo. The residue was diluted with H2O. The aqueous solution was extracted with ethyl acetate. The organic layers were combined and washed with aq.NaHCO3 and brine, dried over Na2SO4, filtered and concentrated to provide the title compound 3d (700 mg, 88%) as a light yellow solid, which was used directly in next step without further purification. 1H NMR (400 MHz, CDCl3) δ7.63 (d, 1H, J=8.5 Hz), 7.57 (d, 1H, J=6.9 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216957B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-b503dfbe286947bc9b160b8fa3abac6f |
| Source note | uspto-grants-2015_12 |