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

HRID 2181868Notes

Reaction equation

HRID 2181868 reaction equation
[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)=[C:21]([F:27])[CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][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])=[C:21]([F:27])[CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224823572-Bromo-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 100951784-[(2-bromo-6-methylphenanthridin-5(6H)-yl)sulfonyl]-2-fluorophenolYield 31.5%

Procedure

The title compound was prepared from 2-bromo-5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.5 g, 1.08 mmol), cyclohexene, (0.27 mL, 3.58 mmol), and 1.0 M boron tribromide in dichloromethane (6.49 mL, 6.49 mmol) according to the procedure and in the same manner as described in Example 4, step b. The crude product was purified by re-crystallization from dichloromethane to yield 4-[(2-bromo-6-methylphenanthridin-5(6H)-yl)sulfonyl]-2-fluorophenol (0.15 g, 0.34 mmol, 31%) as an off-white solid, m.p. 203-206° C.;

Workup

  1. customThe crude product was purified by re-crystallization from dichloromethane

Sources & evidence

ORD record
ord-31e9ee2f557a45828fcc1a723df7ea63
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…