Acetonitrile → 5-Chloro-2-(methylsulfonyl)benzonitrile

HRID 1013954Notes

Reaction equation

HRID 1013954 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](SC)=[C:6]([CH:9]=1)[C:7]#[N:8].O[O:13][S:14]([O-:16])=O.[K+].[C:18](#N)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:14]([CH3:18])(=[O:16])=[O:13])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfite2×HCID 598456935-Chloro-2-(methylthio)benzonitrile

Product 1

HCID 669700485-Chloro-2-(methylsulfonyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

(Step 2) To a solution of 5-chloro-2-(methylsulfanyl)benzonitrile obtained in Step 1 (1.0 g) in acetonitrile (15 ml) was added dropwise a solution of Oxone® (6.98 g) in water (20 ml). The resulting mixture was stirred at room temperature for 5 hr. Oxone® (1.2 g) was added, and the mixture was stirred overnight at room temperature. To the reaction mixture was added water (25 ml), and the resulting mixture was stirred at 0° C. for 3 hr. The precipitate was collected by filtration, washed with water, and dried to give 5-chloro-2-(methylsulfonyl)benzonitrile (0.92 g) as a white solid.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. stirringthe resulting mixture was stirred at 0° C. for 3 hr
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-904ee12190d34f2e873ee609dbd46b2f
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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