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

HRID 2181884Notes

Reaction equation

HRID 2181884 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)=[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

Participants

5

Reactant 4

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

Product 1

HCID 104121424-[(2-bromo-8-chloro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 56.8%

Procedure

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.;

Workup

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

Sources & evidence

ORD record
ord-b6e6f7a08dac4d01abc12f92bf934044
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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