Acetonitrile → HCID 57448066, compound

HRID 2358120Notes

Reaction equation

HRID 2358120 reaction equation
[Br:1][C:2]1[C:3]([F:9])=[C:4](S)[CH:5]=[CH:6][CH:7]=1.I([O-])(=O)(=O)=O.[Na+].[S:16](Cl)(Cl)(=[O:18])=[O:17].[C:21](=O)([O-])[O-].[Na+].[Na+].[C:27](#[N:29])C>[Ru](Cl)(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([F:9])=[C:4]([S:16]([N:29]([CH3:27])[CH3:21])(=[O:18])=[O:17])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 24648Sulfuryl chlorideHCID 23667635Sodium periodateHCID 566046283-Bromo-2-fluorobenzenethiol

Product 1

HCID 57448066HCID 57448066, compound

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-bromo-2-fluorobenzenethiol (1.9 g, 9.2 mmol), sodium periodate (4.8 g, 22.9 mmol) and ruthenium trichloride (5 mg) in acetonitrile (60 ml) was stirred at 0° C. for 5 min. after which sulfonyl chloride (1.9 ml, 22.9 mmol) was added dropwise. The mixture was stirred for an additional hour and ethyl acetate (50 ml) and aqueous sodium carbonate (10%, 50 ml) was added. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). To the combined organic phase, dimethylamine (40% in water, 10 ml) was added and the mixture was stirred for 1 h. Evaporation of the solvents and purification by flash chromatography yielded the title compound (1.1 g). MS m/z (rel. intensity, 70 eV) 283 (M+, 47), 281 (M+, 44), 239 (32), 73 (59), 94 (bp).

Workup

  1. additionwas added dropwise
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  4. additionTo the combined organic phase, dimethylamine (40% in water, 10 ml) was added
  5. stirringthe mixture was stirred for 1 h
  6. customEvaporation of the solvents and purification by flash chromatography

Sources & evidence

ORD record
ord-85e9e7c6bcb2412b89d8df648adbf012
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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