Chlorosuccinimide → HCID 11289654, Verbindung

HRID 1830688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830688
[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, Verbindung

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)
  3. customto yield 0.16 g (84%) of the

Quellen und Nachweise

ORD-Eintrag
ord-2636acf7c04f4f74bfca0e387e78f1aa
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067524B2

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