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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1504946Generated: November 1, 2026

Thiophosgene → 5-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrile

https://huagongshe.com/reaction/1504946

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThiophosgeneHCID 10040—
Reactant4-Amino-5-fluoro-2-(trifluoromethyl)benzonitrileHCID 68292928—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product5-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrileHCID 8671181088%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09216957B2
Source datasetuspto-grants-2015_12
ORD IDord-b503dfbe286947bc9b160b8fa3abac6f
Source noteuspto-grants-2015_12