Sodium methanesulfonate → HCID 22747447, compound

HRID 2246314Notes

Reaction equation

HRID 2246314 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[F:9].[CH3:10][S:11]([O-])(=[O:13])=[O:12].[Na+]>CN(C)C(=O)C.[Cu](I)I>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:11]([CH3:10])(=[O:13])=[O:12])[C:3]=1[F:9]

Participants

5

Reactant 2

HCID 638112Sodium methanesulfonateHCID 190666581,2-Difluoro-3-iodobenzene

Product 1

HCID 22747447HCID 22747447, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 31374DimethylacetamideSolvent

Procedure

1,2-Difluoro-3-iodobenzene (1.70 g; 7.08 mmol), 2.17 g (21.2 mmol) of sodium methanesulfonate and 4.03 g (21.2 mmol) of copper iodide were heated with stirring at 111° C. for 20 hours in 50 ml of N,N-dimethylacetamide. The reaction solution was filtered, chloroform was added to the filtrate and the mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=2:1) to give 987 mg (yield: 72%) of 1,2-difluoro-3-methanesulfonylbenzene as a colorless transparent solution.

Workup

  1. filtrationThe reaction solution was filtered
  2. additionchloroform was added to the filtrate
  3. washthe mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5ebaa3e9af374c4c97da47c985b54541
Source dataset
uspto-grants-2010_03
Patent number
US07687502B2

Reaction notes

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