4-Fluoro-3-methylbenzonitrile → 3-Methyl-4-(methylsulfanyl)benzonitrile

HRID 527372Notes

Reaction equation

HRID 527372 reaction equation
[CH3:1][S-:2].[Na+].F[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[CH3:13]>CN(C=O)C>[CH3:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[S:2][CH3:1])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 27791804-Fluoro-3-methylbenzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 578566063-Methyl-4-(methylsulfanyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium methanethiolate (1.60 g, 22.8 mmol) is added to a solution of 4-fluoro-3-methyl-benzonitrile (2.50 g, 18.5 mmol) in DMF, and the mixture is heated at 80° C. for 15 min. All volatiles are evaporated, and the residue is treated with water. The mixture is extracted with ethyl acetate twice, and the organic layer is dried over Na2SO4 and concentrated. Yield: 3.0 g (99% of theory); ESI mass spectrum: [M+H]+=164; r.t. HPLC: 0.61 min (X011_S03).

Workup

  1. customAll volatiles are evaporated
  2. additionthe residue is treated with water
  3. extractionThe mixture is extracted with ethyl acetate twice
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. customr.t
  7. custom0.61 min (X011_S03)

Sources & evidence

ORD record
ord-7407de6ace15485596ad83621c5bd3c0
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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