Dimethylformamide → 5-Formyl-2-(methylsulfanyl)benzonitrile

HRID 1630774Notes

Reaction equation

HRID 1630774 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([CH:10]=[O:11])=[C:6]([CH:9]=1)C#N.C(=O)([O-])[O-].[K+].[K+].[CH3:18][S-:19].[Na+].C[N:22]([CH:24]=O)C>C(OCC)(=O)C>[CH:10]([C:5]1[CH:4]=[CH:3][C:2]([S:19][CH3:18])=[C:9]([CH:6]=1)[C:24]#[N:22])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 4378561Sodium methanethiolateHCID 202966885-Fluoro-2-formylbenzonitrile

Product 1

HCID 179666355-Formyl-2-(methylsulfanyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask is charged with 5-fluoro-2-formyl-benzonitrile (0.200 g, 1.34 mmol), potassium carbonate (0.371 g, 0.268 mmol), sodium thiomethoxide (0.142 g, 2.01 mmol) and DMF (20 mL). The mixture is stirred at room temperature for 10 min, then diluted with ethyl acetate and washed with water. The organic layer is dried over sodium sulfate and concentrated in vacuo to afford 5-formyl-2-methylsulfanyl-benzonitrile as a yellow color solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.64 (s, 3H), 7.41 (d, J=8.3 Hz, 1H), 8.01 (dd, J=8.5, 1.9 Hz, 1H), 8.07 (d, J=1.8 Hz, 1H), 9.95 (s, 1H).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b1898b320ac443f8375ce7ad2222050
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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