Nitric Acid → 3,3'-Dinitro-4-bromo benzophenone

HRID 640883Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.OS(O)(=O)=O.[N+:24]([O-])([OH:26])=[O:25]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)=[O:9])=[CH:6][C:7]=1[N+:24]([O-:26])=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

The crude (4-bromo-phenyl)-(3-nitro-phenyl)-methanone (11.1 g, 36.27 mmol) was dissolved in dichloroethane (35 mL) and added dropwise via addition funnel to a mixture of concentrated H2SO4(aq) (16 mL, 290 mmol) and fuming HNO3(aq) (13 mL, 290 mmol). The mixture was stirred at 60° C. overnight. Subsequently the mixture was poured over ice water and allowed to stir resulting in precipitation of the product. The product was filtered and dried affording 72% yield of the (4-Bromo-3-nitro-phenyl)-(3-nitro-phenyl)-methanone (9.17 g, 26.1 mmol).

Workup

stirringto stir
customresulting in precipitation of the product
filtrationThe product was filtered
customdried

Sources & evidence

ORD record: ord-2d9520d5a810405caf7df98d5a09019f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692005B2

Reaction notes

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