3-Fluoro-4-formylbenzonitrile → 4-Formyl-3-(methylsulfanyl)benzonitrile

HRID 2361913Notes

Reaction equation

HRID 2361913 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=[O:11])[C:5]#[N:6].[CH3:12][S-:13].[Na+]>CS(C)=O.O>[CH:10]([C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[S:13][CH3:12])=[O:11]

Participants

5

Reactant 2

HCID 27831503-Fluoro-4-formylbenzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 581337424-Formyl-3-(methylsulfanyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

3-Fluoro-4-formylbenzonitrile (2.00 g, 13.4 mmol) was dissolved in DMSO (27 ml), and sodium methanethiolate (1.50 g, 21.5 mmol) was added with ice-bath cooling. The mixture was stirred for 45 min and then diluted with water (100 ml). The resulting precipitated product was filtered off with suction, washed with water and dried under reduced pressure. This gave 1.36 g (51% of theory) of the target compound as a yellow crystalline solid.

Workup

  1. temperaturecooling
  2. customThe resulting precipitated product
  3. filtrationwas filtered off with suction
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-34ac237b97314e41992f3b40dcd0748b
Source dataset
uspto-grants-2014_04
Patent number
US08691817B2

Reaction notes

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