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

HRID 2181875Notes

Reaction equation

HRID 2181875 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([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][C:4]=1[CH3:28].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH3:9][C:8]1[CH:7]=[C:6]([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]=[C:4]([CH3:28])[C:3]=1[OH:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224823695-[(4-Methoxy-3,5-dimethylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 99997662,6-dimethyl-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 82%

Procedure

The title compound was prepared from 5-[(4-methoxy-3,5-dimethylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (1.0 g, 2.54 mmol), cyclohexene (0.64 mL, 6.36 mmol) and 1.0 M boron tribromide in dichloromethane (15.3 mL, 15.3 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 2,6-dimethyl-4-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol (0.79 g, 2.08 mmol, 82%) as a white solid, m.p. 211-213° C.;

Workup

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

Sources & evidence

ORD record
ord-e9182468a997495cb775bd17be93df73
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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