Dichloromethane → HCID 10407769, compound

HRID 2181882Notes

Reaction equation

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

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 22482264HCID 22482264, compound

Product 1

HCID 10407769HCID 10407769, compoundYield 42%

Procedure

The title compound was prepared from 8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.6 g, 1.50 mmol), cyclohexene (0.304 mL, 3.75 mmol), and 1.0 M boron tribromide in dichloromethane (9.0 mL, 9.0 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-[(8-chloro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.24 g, 0.63 mmol, 42%) as a white solid, m.p. 176-178° C.;

Workup

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

Sources & evidence

ORD record: ord-96067dd283054e5c93550d01ddc9edf9
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894061B2

Reaction notes

Loading…