4-Fluoroiodobenzene → 1-Fluoro-4-(phenylsulphonyl)benzene

HRID 2179307Notes

Reaction equation

HRID 2179307 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9]1([S:15]([O-:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+]>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 96054-FluoroiodobenzeneHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 675561-Fluoro-4-(phenylsulphonyl)benzeneYield 29.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 1-fluoro-4-iodobenzene (448 mg, 2.00 mmol) and sodium benzenesulfinate (755 mg, 1.50 mmol) in DMF (5 mL) under a nitrogen atmosphere was added copper (I) trifluoromethanesulfonate benzene complex (443 mg, 2.70 mmol). The reaction was stirred at 65° C. overnight, diluted with ethyl acetate then washed with water and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the crude material which was purified by flash column chromatography (85:15 to 80:20 hexanes/ethyl acetate) to give 1-fluoro-4-(phenylsulfonyl)-benzene (103 mg, 22%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.99-7.92 (m, 4H), 7.58-7.49 (m, 3H), 7.18 (t, J=8.4 Hz, 1H), 7.21-7.15 (m, 1H).

Workup

  1. additionwas added copper (I) trifluoromethanesulfonate benzene complex (443 mg, 2.70 mmol)
  2. washthen washed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude material which
  6. customwas purified by flash column chromatography (85:15 to 80:20 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e63d8033a16748e7a64eb05cfe47fe1e
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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