Nitric Acid → 4-Bromo-3,4'-dinitro benzophenone

HRID 640845Notes

Reaction equation

HRID 640845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][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][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:9])=[CH:6][C:7]=1[N+:24]([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 28256634-Bromo-4'-nitrobenzophenone

Product 1

HCID 197081834-Bromo-3,4'-dinitro benzophenoneYield 78%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

The crude (4-Bromo-phenyl)-(4-nitro-phenyl)-methanone (15 g, 49 mmol) was dissolved in 45 mL of dichloroethane and added dropwise via addition funnel to a mixture of concentrated H2SO4(aq) (21 mL, 392 mmol) and fuming HNO3(aq) (15.7 mL, 392 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 78% yield of the desired (4-Bromo-3-nitro-phenyl)-(-4-nitro-phenyl)-methanone (13.1 g, 38 mmol).

Workup

  1. stirringto stir
  2. customresulting in precipitation of the product
  3. filtrationThe product was filtered
  4. customdried

Sources & evidence

ORD record
ord-22777fe18cbf410abb95fb7b59eb9416
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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