2,8-Dibromo-3,7-dinitrodibenzothiophene-5-oxide → Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxide

HRID 376731Notes

Reaction equation

HRID 376731 reaction equation
[Br:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[S:6](=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.BrC1C([N+]([O-])=O)=CC2S(=[O:36])C3C=CC(Br)=CC=3C=2C=1.I([O-])(=O)(=O)=O.[Na+]>[Ru](Cl)(Cl)Cl.O.O1CCCC1.C(#N)C.O1CCOCC1.C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[S:6](=[O:36])(=[O:17])[C:7]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Br:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

Participants

10

Reactant 3

HCID 158859092,8-Dibromo-3,7-dinitrodibenzothiophene-5-oxideHCID 158859102,8-Dibromo-3-nitrodibenzothiophene-5-oxideHCID 23667635Sodium periodate

Product 1

HCID 4571975Dibenzothiophene, 2,8-dibromo-3,7-dinitro-, 5,5-dioxide

Reagents, catalysts & solvents 6

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolvent3×HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

Referring to Scheme II, a mixture of 2,8-dibromo-3,7-dinitrodibenzothiophene-5-oxide 3a and 2,8-dibromo-3-nitrodibenzothiophene-5-oxide 3b was treated in a heterogeneous solvent mixture which include but not limited to acetonitrile, carbon tetrachloride and water, p-dioxane and water, acetonitrile, tetrahydrofuran and water; with an oxidizing agent which include but not limited to sodium periodate and ruthenium(III) chloride; stirred at a temperature range from 15-75° C. until completion as indicated by TLC to yield 2,8-dibromo-3,7-dinitrodibenzothiophene-5,5-dioxide 9 as the isolated product. Treating 2,8-dibromo-3,7-dinitrodibenzothiophen-5,5-dioxide 9 with a reducing agent which include but are not limited to powdered iron, tin (II) chloride, zinc metal or palladium on charcoal with hydrogen in alcoholic solvents which include but are not limited to methyl alcohol, ethyl alcohol, propyl alcohol or 2-methoxy-ethanol and the like; and an organic acid which includes but is not limited to acetic acid; at a temperature range from 50-120° C. for about 2 hours or until completion to give 2,8-dibromo-5,5-dioxo-5H-5λ6 -dibenzothiophene-3,7-diamine 10.

Workup

  1. additionwas treated in a heterogeneous solvent mixture which

Sources & evidence

ORD record
ord-15bd87a547b04673893d78ec055368d6
Source dataset
uspto-grants-2000_02
Patent number
US06022307

Reaction notes

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