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

HRID 1720578Notes

Reaction equation

HRID 1720578 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:10][S:11](O)(=[O:13])=[O:12]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:11]([Cl:10])(=[O:13])=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 10329DihydrobenzofuranHCID 24638Chlorosulfonic acid

Product 1

HCID 27761542,3-Dihydrobenzofuran-5-sulfonyl ChlorideYield 30.2%

Procedure

2,3-dihydrobenzofuran (6.0 g, 49.94 mmol) is added over 20 minutes to chlorosulfonic acid (29.09 g, 249.69 mmol) at -20° C. The reaction mixture is quenched by addition of ice followed by water (20 mL). The mixture is then extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (30% ethyl acetate/hexane) to give 2,3-dihydrobenzofuran-5-sulfonyl chloride (3.3 g).

Workup

  1. customThe reaction mixture is quenched by addition of ice
  2. extractionThe mixture is then extracted with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is evaporated
  6. customThe crude product is purified by silica gel chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b655d706daae4c408854c1d74fdd63cd
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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