Methyl iodide → 1,3-Difluoro-5-(methylsulfanyl)benzene

HRID 1499549Notes

Reaction equation

HRID 1499549 reaction equation
CI.[F:3][C:4]1[CH:5]=[C:6]([SH:11])[CH:7]=[C:8]([F:10])[CH:9]=1.[C:12](=O)([O-])[O-].[K+].[K+]>CC#N>[F:3][C:4]1[CH:5]=[C:6]([S:11][CH3:12])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27583613,5-Difluorothiophenol

Product 1

HCID 187113611,3-Difluoro-5-(methylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Methyl iodide (2.91 g, 20.5 mmol) was added dropwise to a stirred mixture of 3,5-difluorobenzenethiol (2.00 g, 13.7 mmol) and potassium carbonate (5.67 g, 41.0 mmol) in dry MeCN (24 mL) at room temperature. The reaction mixture was stirred at 80° C. for 2 h. After cooling, the mixture was filtered under vacuum, washed with MeCN and concentrated under reduced pressure to give the sub-title compound, which was used directly in the next step without further purification (1.74 g, 80%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered under vacuum
  3. washwashed with MeCN
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a9dd3446c664da4be4cebcf06a12dd7
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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