Bromine → 2-Bromo-8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

HRID 2181883Notes

Reaction equation

HRID 2181883 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][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:27].[Br:28]Br>C(O)(=O)C>[Br:28][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH:5]([CH3:27])[C:4]3[C:13](=[CH:14][CH:15]=[C:2]([Cl:1])[CH:3]=3)[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 22482264HCID 22482264, compound

Product 1

HCID 224823272-Bromo-8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridineYield 61.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared from 8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.95 g, 2.38 mmol), bromine (0.12 mL, 9.50 mmol), and glacial acetic acid (24 mL) according to the procedure and in the same manner as described in Example 4, step a. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:3 to 1:1 gradient) to yield 2-bromo-8-chloro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.70 g, 1.46 mmol, 61%) as a white solid;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:3 to 1:1 gradient)

Sources & evidence

ORD record
ord-0af10b7054634edea15ca83ab096a2de
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…