Phosphorus oxychloride → 8-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-sulfonyl chloride

HRID 1166863Notes

Reaction equation

HRID 1166863 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:14]([OH:17])(=O)=[O:15].P(Cl)(Cl)([Cl:20])=O>>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:14]([Cl:20])(=[O:17])=[O:15]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 522803Dibenzofuran-2-sulphonic acid

Product 1

HCID 27580308-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-sulfonyl chlorideYield 85%

Procedure

2-Dibenzofuransulfonic acid (12.8 mmol) was heated at 70° C. with phosphorus oxychloride (1.30 ml, 14.0 mmol) for 2 h. Excess phosphorus oxychloride was removed under reduced pressure. The residue was decomposed with ice water and extracted with ethyl acetate. The extract was washed with 5% sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated to yield 2.9 g crude 2-dibenzofuransulfonyl chloride.

Workup

  1. customExcess phosphorus oxychloride was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 5% sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dea789a86914408d9514dc9cbedea2e6
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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