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

HRID 640956Notes

Reaction equation

HRID 640956 reaction equation
OS(O)(=O)=O.[N+:6]([O-])([OH:8])=[O:7].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)=[O:18])=[CH:13][CH:12]=1>>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)=[O:18])=[CH:15][C:16]=1[N+:6]([O-:8])=[O:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 123219594-Bromo-3'-nitrobenzophenone

Product 1

HCID 197081953,3'-Dinitro-4-bromo benzophenone

Procedure

A 2 L, 3 necked round bottomed flask equipped with a mechanical stirrer, thermocouple and ice-bath was charged with concentrated H2SO4(aq) (635 mL) and concentrated HNO3(aq) (62 mL). The flask and its contents were cooled to 0° C. (4-Bromo-phenyl)-(3-nitro-phenyl)-methanone (127 g, 0.42 mol) was added over a period of 1 h and the temperature was kept under 10° C. Thirty minutes later, the reaction was complete by thin layer chromatographic analysis (Hexanes/EtOAc 6:4). The reaction was poured into ice-H2O (2 L). The solids were filtered, washed with H2O (4 L), saturated NaHCO3(aq) (1 L) and an additional portion of H2O (1 L). The product was dried at 45° C., for 48 h yielding (4-Bromo-3-nitro-phenyl)-(3-nitro-phenyl)-methanone in 95% (138.4 g, 0.39 mol).

Workup

  1. customA 2 L, 3 necked round bottomed flask equipped with a mechanical stirrer
  2. additionwas added over a period of 1 h
  3. customwas kept under 10° C
  4. customThirty minutes
  5. filtrationThe solids were filtered
  6. washwashed with H2O (4 L), saturated NaHCO3(aq) (1 L)
  7. customThe product was dried at 45° C., for 48 h

Sources & evidence

ORD record
ord-3d24776c40444433bb11903ec0c5061b
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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