Sulfuric Acid → 1-Bromo-3,5-dinitrobenzene

HRID 1028100Notes

Reaction equation

HRID 1028100 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.C1C(=O)N([Br:25])C(=O)C1>>[Br:25][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 74521,3-DinitrobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 445341-Bromo-3,5-dinitrobenzeneYield 96%

Conditions

Temperature
60 °C

Procedure

1,3-Dinitrobenzene (25 g, 149 mmol) was dissolved in sulfuric acid (44.5 mL, 835 mmol) and NBS (31.8 g, 178 mmol) was added. The mixture was stirred at 60° C. for 2 days. The reaction was cooled to ambient temperature and the mixture was poured into ice water to form a precipitate. The product was collected by filtration, washed with water and hexanes to yield 35.1 g (142 mmol, 96%) of 1-bromo-3,5-dinitrobenzene as a beige solid.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customto form a precipitate
  3. filtrationThe product was collected by filtration
  4. washwashed with water and hexanes

Sources & evidence

ORD record
ord-22469cee974544af9e8cc99e75bcf366
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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