Triphenylphosphine → (E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonyl chloride

HRID 2283260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283260
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:25]1[C:30]2=[CH:31][CH:32]=[CH:33][C:29]2=[CH:28][CH:27]=[C:26]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1/[CH:40]=[CH:41]/S(O)(=O)=O>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:25]1[C:30]2=[CH:31][CH:32]=[CH:33][C:29]2=[CH:28][CH:27]=[C:26]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1/[CH:40]=[CH:41]/[S:1]([Cl:5])(=[O:3])=[O:2]

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 24648Sulfuryl chlorideHCID 86632001(E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonic acid

Produkt 1

HCID 86632000(E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonyl chlorideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sulfurylchloride (0.21 mL, 2.6 mmol) was added to a solution of triphenylphosphine (0.68 g, 2.5 mmol) in CH2Cl2 (10 mL) at 0° C. The ice-bath was then removed and (E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonic acid (0.38 g, 1.18 mmol) was added and the resulting mixture was stirred for 6 h at RT. A catalytic amount of tetrabutyl ammonium iodide was added and the reaction was stirred for an additional 12 h. The mixture was then filtered and the filtrate was concentrated in vacuo and the product was purified by column chromatography eluting with 20% EtOAc/hexanes to give the product as a yellow solid (0.27 g, 73%).

Aufarbeitung

  1. customThe ice-bath was then removed
  2. stirringthe reaction was stirred for an additional 12 h
  3. filtrationThe mixture was then filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe product was purified by column chromatography
  6. washeluting with 20% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9b3165df355a465ab96e5cdf49e96acc
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145380B2

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