Dichloromethane → HCID 10479453, Verbindung

HRID 2181845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181845
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=3)[C:4]=2[CH:3]=1.B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=3)[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 224823412-Bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine

Produkt 1

HCID 10479453HCID 10479453, VerbindungAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67553Tetrabutylammonium IodideKatalysator

Versuchsvorschrift

The title compound was prepared from 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.61 g, 1.3 mmol), tetrabutylammonium iodide (1.1 g, 3.1 mmol), and 1 M boron trichloride in dichloromethane (9.0 mL, 9.0 mmol) according to the procedure and in the same manner as described in Example 35, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient), followed by trituration from a mixture of ethyl acetate-hexane to yield 4-[(2-bromo-6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.23 g, 38%), m.p. 220-221° C.;

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (3:7 to 1:1 gradient)
  3. additionfollowed by trituration from a mixture of ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-26909878c1284a91b52af24322c49309
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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