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

HRID 2064317Notes

Reaction equation

HRID 2064317 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; Example 8A) 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-ea32d8708e2c48f49a0865f915074332
Source dataset
uspto-grants-2012_10
Patent number
US08288402B2

Reaction notes

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