Phosphorus pentachloride → 4-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

HRID 1251472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251472
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([O-])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:22]>C(Cl)Cl>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:22])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24819Phosphorus pentachlorideHCID 23701365Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

Produkt 1

HCID 181794244-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a slurry of sodium 4-(4-fluorobenzyloxy)benzenesulfonate (0.5 grams, 1.64 mmole), in methylene chloride (5 mL) was added phosphorus pentachloride (275 mg, 1.31 mmole). The resulting mixture was heated at reflux for 7 hours. After cooling in an ice bath and quenching with water (15 mL), the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and concentrated to afford 4-(4-fluorobenzyloxy)benzenesulfonyl chloride a white solid (130 mg, 26%).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 7 hours
  3. temperatureAfter cooling in an ice bath
  4. customquenching with water (15 mL)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82465305d0684920acb70038144f1704
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342521B1

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