Thiophenol → 3-Fluoro-2-phenylthio-5-trifluoromethylpyridine

HRID 2229119Notes

Reaction equation

HRID 2229119 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[C:13]1([SH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.[Cu]>[F:8][C:7]1[C:2]([S:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

5

Reactant 2

HCID 7969ThiophenolHCID 134215472,3-Difluoro-5-(trifluoromethyl)pyridine

Product 1

HCID 184665183-Fluoro-2-phenylthio-5-trifluoromethylpyridine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

Over a period of 2.5 h, 59.6 g (0.326 mol) of 2,3-difluoro-5-trifluoromethylpyridine were added at 148-156° C. to 37.7 g (0.338 mol) of 98.7% pure thiophenol and 2.1 mg (0.01 mol %) of copper powder, and the mixture was stirred at 156-164° C. for 2 hours. After cooling, the residue was taken up in methylene chloride, washed with 0.5 N of aqueous sodium hydroxide solution and with water, dried over magnesium sulfate and concentrated under reduced pressure. 88.9 g (100% of theory) of the title compound of n24/D=1.5539 were obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed with 0.5 N of aqueous sodium hydroxide solution and with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1318a437b8b648be8b3e5dd013d7ff0b
Source dataset
uspto-grants-2002_07
Patent number
US06420314B1

Reaction notes

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