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

HRID 2181872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181872
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:25]([CH3:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]2=3)(=[O:11])=[O:10])=[CH:5][C:4]=1[C:27]([F:30])([F:29])[F:28].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH3:26][CH:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]1[S:9]([C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[C:4]([C:27]([F:29])([F:28])[F:30])[CH:5]=1)(=[O:10])=[O:11]

Komponenten

5

Edukt 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482395HCID 22482395, Verbindung

Produkt 1

HCID 104547554-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]-2-(trifluoromethyl)phenolAusbeute 9 %

Versuchsvorschrift

The title compound was prepared from 5-{[4-methoxy-3-(trifluoromethyl)phenyl]sulfonyl}-6-methyl-5,6-dihydrophenanthridine (0.5 g, 1.15 mmol), cyclohexene (0.29 mL, 2.88 mmol), and 1.0 M boron tribromide in dichloromethane (6.92 mL, 6.92 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-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]-2-(trifluoromethyl)phenol (0.044 g, 0.104 mmol, 9%) as an off-white 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-f5bb230fbc3c4671a4736c96639b5a2d
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894061B2

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