Phosphorus pentachloride → 2-Chloro-5-(1-chloro-3-oxo-1,3-dihydro-2-benzofuran-1-yl)benzene-1-sulfonyl chloride

HRID 2059135Notes

Reaction equation

HRID 2059135 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:11])[O:9]2)=[CH:4][C:3]=1[S:18]([Cl:21])(=[O:20])=[O:19].P(Cl)(Cl)(Cl)(Cl)[Cl:23]>ClC1C=CC=CC=1>[Cl:23][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:18]([Cl:21])(=[O:20])=[O:19])[CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](=[O:11])[O:9]1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 13041924HCID 13041924, compound

Product 1

HCID 30178672-Chloro-5-(1-chloro-3-oxo-1,3-dihydro-2-benzofuran-1-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a preferred procedure, 3-(4'-chloro-3'-chlorosulfonylphenyl)phthalide (17.15 g) and phosphorous pentachloride (104 g.) is heated under reflux for 2.5 hours in 300 ml of chlorobenzene. The cooled solution is extracted three times with 100 ml portions of water, dried (Na2SO4), filtered, and concentrated under a reduced pressure to give a yellow oil from which the title compound can be fractionally crystallized.

Workup

  1. extractionThe cooled solution is extracted three times with 100 ml portions of water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-627f93794d0f4184b069ffcc71635d9d
Source dataset
uspto-grants-1982_03
Patent number
US04322356

Reaction notes

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