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

HRID 2181884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181884
[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]([CH3:27])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([Cl:28])[CH:9]=3)[C:4]=2[CH:3]=1.C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[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]([CH3:27])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([Cl:28])[CH:9]=3)[C:4]=2[CH:3]=1

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224823272-Bromo-8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Produkt 1

HCID 104121424-[(2-bromo-8-chloro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolAusbeute 56,8 %

Versuchsvorschrift

The title compound was prepared from 2-bromo-8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.6 g, 1.25 mmol), cyclohexene (0.32 mL, 3.13 mmol), and 1.0 M boron tribromide in dichloromethane (7.52 mL, 7.52 mmol) according to the procedure and in the same manner as described in Example 1, step b. The crude product was purified by flash column chromatography on silica gel, eluting with dichloromethane to yield 4-[(2-bromo-8-chloro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.33 g, 0.71 mmol, 56%) as a light-yellow solid, m.p. 213-215° C.;

Aufarbeitung

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b6e6f7a08dac4d01abc12f92bf934044
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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