Sulfuryl chloride → Furan-3-sulfonyl chloride

HRID 1081341Notes

Reaction equation

HRID 1081341 reaction equation
Br[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.C([Li])CCC.[S:12](Cl)([Cl:15])(=[O:14])=[O:13]>O1CCCC1.C(OCC)C>[O:3]1[CH:4]=[CH:5][C:6]([S:12]([Cl:15])(=[O:14])=[O:13])=[CH:2]1

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 2776190Furan, 2-bromo-HCID 178418339Butyllithium

Product 1

HCID 22179302Furan-3-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In flame dried glassware under a nitrogen atmosphere to a solution of 428 mg (2.909 mmol) of 3 bromofuran in anhydrous tetrahydrofuran at -78° C. was added 2.0 mL n-butyl lithium (3.2 mmol at 1.6 molar in hexane). After 45 minutes the resultant solution was added via cannula to a 20° C. solution of sulfuryl chloride in diethyl ether (5 mL plus a 2 mL rinse). After 1 h, the reaction was quenched with 0.5N hydrochloric acid and extraced into diethyl ether. The ethereal extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 158 mg of the title product. (1H) NMR (CDCl3) consistent with structure.

Workup

  1. temperatureIn flame
  2. washa 2 mL rinse)
  3. customthe reaction was quenched with 0.5N hydrochloric acid
  4. washThe ethereal extracts were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d76577d730304b15970cba0cf665fac2
Source dataset
uspto-grants-1996_12
Patent number
US05585397

Reaction notes

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