Hydrochloric Acid → Pentafluorophenyl 4-[(phenylmethyl)oxy]benzenesulfonate

HRID 130432

Reaktionsgleichung

Reaktionsgleichung von HRID 130432
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:26][C:27]1[C:32]([OH:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=1[F:37].Cl>ClCCl>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([O:33][C:32]3[C:27]([F:26])=[C:28]([F:37])[C:29]([F:36])=[C:30]([F:35])[C:31]=3[F:34])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Produkt 1

HCID 59007064Pentafluorophenyl 4-[(phenylmethyl)oxy]benzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

To a stirred solution of 4-[(phenyhnethyl)oxy]benzenesulfonyl chloride (D48) (13.77 g, 48.70 mmol) in dichloromethane (265 ml) was added triethylamine (9.16 ml, 65.75 mmol) under argon and the mixture cooled to −15° C. A solution of pentafluorophenol (9.86 g, 53.57 mmol) in dichloromethane (20 ml+20 ml wash) was then added quickly and the reaction allowed to wami slowly to room temperature over 1.75 h. Hydrochloric acid (2M, 250 ml) was then added and the mixture stirred for 20-30 min and the layers separated. The aqueous layer was then re-extracted with dichloromethane (100 ml) and the combined organic fractions washed with saturated aqueous sodium hydrogen carbonate (200 ml). The layers were separated and the aqueous re-extracted with dichloromethane (100 ml). All the dichloromethane layers were combined and dried over sodium sulfate, filtered and evaporated. The resulting solid was then dissolved in dichloromethane (40 ml) with warming, and allowed to cool and then purified by chromatography on silica gel eluting with 10-15% diethyl ether/hexane to afford the title compound (D49). 1H-NMR (d6-DMSO) d 7.97-7.94 (2H, m), 7.50-7.31 (7H, m), 5.29 (2H, s).

Aufarbeitung

  1. customthe layers separated
  2. extractionThe aqueous layer was then re-extracted with dichloromethane (100 ml)
  3. washthe combined organic fractions washed with saturated aqueous sodium hydrogen carbonate (200 ml)
  4. customThe layers were separated
  5. extractionthe aqueous re-extracted with dichloromethane (100 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe resulting solid was then dissolved in dichloromethane (40 ml)
  10. temperaturewith warming
  11. temperatureto cool
  12. custompurified by chromatography on silica gel eluting with 10-15% diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6c7576c8889e4184bf20253481c4a9c9
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381728B2

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