Phosphorus pentachloride → HCID 22645095, compound

HRID 2084870Notes

Reaction equation

HRID 2084870 reaction equation
[Na+].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([O-:22])(=O)=[O:20])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:24]>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([Cl:24])(=[O:22])=[O:20])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 88000559HCID 88000559, compound

Product 1

HCID 22645095HCID 22645095, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonic acid sodium salt (2.81 g, 8.7 mmol) was added 2.8 g of phosphorous pentachloride and 50 mL of dichloromethane. The reaction warmed to 40° followed by dissolution of the reagents. The reaction was then quenched with ice, extracted with dichloromethane, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified via flash chromatography using 20:1 Hex:EtOAc to afford 0.5 g (17%) of 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonyl chloride.

Workup

  1. temperatureThe reaction warmed to 40°
  2. dissolutionfollowed by dissolution of the reagents
  3. customThe reaction was then quenched with ice
  4. extractionextracted with dichloromethane
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting oil was purified via flash chromatography

Sources & evidence

ORD record
ord-ad8c376ed0c143d3ae1d0d9d56d31e87
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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