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

HRID 264283Notes

Reaction equation

HRID 264283 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-ccdf8f812d024797a79fa6539e83a5c5
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

Loading…