Dichloromethane → 2-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181849
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([Cl:29])[CH:22]=1)(=[O:20])=[O:19])[CH3:2].B(Cl)(Cl)Cl.ClCCl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:29][C:23]1[CH:22]=[C:21]([S:18]([N:4]2[CH:3]([CH2:1][CH3:2])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=3)[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=3)(=[O:19])=[O:20])[CH:26]=[CH:25][C:24]=1[OH:27]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 22482342HCID 22482342, Verbindung

Produkt 1

HCID 99793892-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenolAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67553Tetrabutylammonium IodideKatalysator

Versuchsvorschrift

The title compound was prepared from 6-ethyl-8-fluoro-5-[(3-chloro-4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (0.41 g, 0.96 mmol), tetrabutylammonium iodide (0.85 g, 2.3 mmol), and 1 M boron trichloride in dichloromethane (6.7 mL, 6.7 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 (20:80 to 35:65 gradient), followed by re-crystallization from a mixture of ethyl acetate-hexane, to yield 2-chloro-4-[(6-ethyl-8-fluorophenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.16 g, 41%), m.p. 174-177° C.;

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (20:80 to 35:65 gradient)
  3. customfollowed by re-crystallization from a mixture of ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-7085b43db0144f709e81e423c66ba17a
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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