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

Reaction equation

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

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 224822965-[(3-Fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 224822772-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 74%

Procedure

The title compound was prepared from 5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.5 g, 1.3 mmol), cyclohexene (0.33 mL, 3.25 mmol) and 1.0 M boron tribromide in dichloromethane (7.8 mL, 7.8 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 sequentially with dichloromethane and ethyl acetate to yield 2-fluoro-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.35 g, 0.96 mmol, 74%) as a light-yellow solid, m.p. 172-174° C.;