Triethylamine → 4-(Biphenyl-2-yloxy)-3-cyano-benzenesulfonic acid pentafluorophenyl ester

HRID 1692251

Reaktionsgleichung

Reaktionsgleichung von HRID 1692251
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][C:9]=1[C:18]#[N:19].[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].CCN(CC)CC>ClCCl>[F:26][C:27]1[C:32]([O:33][S:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:9]([C:18]#[N:19])[CH:10]=2)(=[O:16])=[O:15])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=1[F:37]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 594365064-(Biphenyl-2-yloxy)-3-cyanobenzenesulfonyl chloride

Produkt 1

HCID 594364764-(Biphenyl-2-yloxy)-3-cyano-benzenesulfonic acid pentafluorophenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 4-(biphenyl-2-yloxy)-3-cyano-benzenesulfonyl chloride (Preparation 55, 500 mg, 1.35 mmol) in dichloromethane (5 ml) was added slowly to pentafluorophenol (249 mg, 1.35 mmol) and Et3N (137 mg, 1.35 mmol) in dichloromethane (5 ml) and stirring continued overnight at ambient temperature. The reaction was concentrated in vacuo and purified using silica gel column chromatography (dichloromethane/heptane 40/60, then 60/40, then 80/20, then dichloromethane) to furnish the title compound. LCMS Rt=1.92 minutes 1H NMR (400 MHz; CDCl3) δ (ppm): 6.69 (d, J=8.98 Hz, 1 H) 7.21-7.30 (m, 2 H) 7.31-7.38 (m, 2 H) 7.43-7.53 (m, 4 H) 7.53-7.58 (m, 1 H) 7.79 (dd, J=8.98, 2.34 Hz, 1 H) 8.06 (d, J=2.34 Hz, 1 H) 19F NMR (376 MHz, CDCl3) δ (ppm): 160.82 (t, J=19.50 Hz) −154.87 (t, J=21.80 Hz) −151.09 (d, J=17.21 Hz)

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-1376d09a6eb94116b1eca581b1020bcb
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153814B2

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