Dichloromethane → HCID 10067413, compound

HRID 2181878Notes

Reaction equation

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

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8079Cyclohexene

HCID 25134Boron tribromide

HCID 22482338HCID 22482338, compound

Product 1

HCID 10067413HCID 10067413, compoundYield 54%

Procedure

The title compound was prepared from 5-[(4-methoxyphenyl)sulfonyl]-6,8-dimethyl-5,6-dihydrophenanthridine (0.6 g, 1.58 mmol), cyclohexene (0.4 mL, 3.95 mmol), and 1.0 M boron tribromide in dichloromethane (9.5 mL, 9.49 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-[(6,8-dimethylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.31 g, 0.85 mmol, 54%) as a white solid, m.p. 111-113° C.;

Workup

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

Sources & evidence

ORD record: ord-a914290567e04ae9974c95381ee67a3d
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894061B2

Reaction notes

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