Methyl iodide → 1,2,4-Trifluoro-5-(methylsulfonyl)benzene

HRID 407870Notes

Reaction equation

HRID 407870 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10]([OH:12])=[O:11].IC.[CH2:15](N(C(C)C)C(C)C)C>CN(C=O)C>[F:9][C:5]1[CH:4]=[C:3]([S:10]([CH3:15])(=[O:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 572413752,4,5-Trifluorobenzenesulfinic acid

Product 1

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4,5-trifluorobenzenesulfinic acid (34 g, 173 mmol), in DMF (200 mL), was added iodomethane (21.6 mL, 347 mmol), and N-ethyl-N-isopropylpropan-2-amine (60.5 mL, 347 mmol). The reaction mixture was stirred overnight at ambient temperature. The reaction was concentrated and partitioned between water and ethyl acetate and extracted with CH2Cl2. The combined organic layers were concentrated and purified over silica gel (15-100% EtOAc in hexanes) to afford 1,2,4-trifluoro-5-(methylsulfonyl)benzene (25.8 g, 123 mmol, 71% yield) as yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between water and ethyl acetate
  3. extractionextracted with CH2Cl2
  4. concentrationThe combined organic layers were concentrated
  5. custompurified over silica gel (15-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4d3484d721434e5da22963726d069d9d
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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