1,3-Dinitrobenzene → 1-Bromo-3,5-dinitrobenzene

HRID 541579

Reaction equation

HRID 541579 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].[Br:13]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:9]=[C:8]([Br:13])[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74521,3-DinitrobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 445341-Bromo-3,5-dinitrobenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

m-Dinitrobenzene (5.0 g, 0.030 mol) was stirred in sulfuric acid (50 mL) and heated to 85° C. N-Bromosuccinimide (5.0 g, 0.030 mol) was added in portions over 1.5 hours while maintaining a temperature of 85° C. The cooled mixture was poured into ice water and the precipitate was collected, washed with water and recrystallized from methanol to give the desired compound (5.9 g, 80%). LCMS for C6H4BrN2O4 (M+H)+: m/z=248.1.

Workup

  1. temperaturewhile maintaining a temperature of 85° C
  2. customthe precipitate was collected
  3. washwashed with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-849f0c1eecfe4953b903c2eca6b00d16
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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