Dihydrobenzofuran → 2,3-Dihydrobenzofuran-5-sulfonyl Chloride

HRID 1957395Notes

Reaction equation

HRID 1957395 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1>CN(C)C=O>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:14][C:9]=2[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 10329DihydrobenzofuranHCID 24648Sulfuryl chloride

Product 1

HCID 27761542,3-Dihydrobenzofuran-5-sulfonyl ChlorideYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 3.35 g of dimethylformamide, at 0° C. under an atmosphere of nitrogen, added 6.18 g of sulfuryl chloride. The mixture was stirred 15 min and treated with 4.69 g of 2,3-dihydrobenzofuran. The mixture was then heated at 100° C. for 1.5 h, cooled to about 40° C., poured onto ice, extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated in vacuo. The residue was taken up in ethyl acetate, cooled to 5° C. for 16 h, and the resultant pink crystals collected by vacuum filtration to provide 6.12 g of the title product. TLC: Rf=0.41, 10% ethyl acetate in hexane. (1H)-NMR (CDCl3) consistent with structure.

Workup

  1. temperaturecooled to about 40° C.
  2. additionpoured onto ice
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. temperaturecooled to 5° C. for 16 h
  8. filtrationthe resultant pink crystals collected by vacuum filtration

Sources & evidence

ORD record
ord-613d6fe38cf341b7990c507bde000e30
Source dataset
uspto-grants-1998_07
Patent number
US05783701

Reaction notes

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