Chlorosuccinimide → HCID 11289654, Verbindung

HRID 895243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895243
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.C1C(=O)N([Cl:28])C(=O)C1>C1COCC1>[Cl:28][C:10]1[C:11]2[C:6](=[CH:5][C:4]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:3][C:2]=2[F:1])[CH:7]=[CH:8][C:9]=1[OH:12]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 11311694HCID 11311694, Verbindung

Produkt 1

HCID 11289654HCID 11289654, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 8-fluoro-6-(4-methoxyphenyl)-2-naphthol (0.17 g, 0.63 mmol) and NCS (0.10 g, 0.76 mmol) in THF (20 mL) were stirred under nitrogen at room temperature overnight according to Method C. The solution was concentrated onto Florosil and purified on a silica column (20% ethyl acetate—hexanes) to yield 0.16 g (84%) of the title compound as a yellow solid. An analytical sample was further prepared by preparative reverse phase HPLC to yield a light yellow solid: mp 120-124° C.; 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.06 (2H, d, J=8.80 Hz), 7.34 (1H, d, J=8.91 Hz), 7.67 (1H, dd, J=1.69 Hz, J=15.48 Hz), 7.78 (2H, d, J=8.78 Hz), 8.01 (1H, d, J=1.54 Hz), 10.62 (1H, s); MS (ESI) m/z 301/303 (M−H)−.

Aufarbeitung

  1. concentrationThe solution was concentrated onto Florosil
  2. custompurified on a silica column (20% ethyl acetate—hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3f878507f10b4e8692fea71d71c53729
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914074B2

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