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

HRID 1504946Notes

Reaction equation

HRID 1504946 reaction equation
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](Cl)(Cl)=[S:16]>C1COCC1.O>[F:10][C:9]1[C:2]([N:1]=[C:15]=[S:16])=[CH:3][C:4]([C:11]([F:14])([F:12])[F:13])=[C:5]([CH:8]=1)[C:6]#[N:7]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 682929284-Amino-5-fluoro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 867118105-Fluoro-4-isothiocyanato-2-(trifluoromethyl)benzonitrileYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washwashed with aq
  5. dry with materialNaHCO3 and brine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b503dfbe286947bc9b160b8fa3abac6f
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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