Hydrogen Bromide → 1-Bromo-2,3-dinitrobenzene

HRID 558445Notes

Reaction equation

HRID 558445 reaction equation
[N+:1]([C:4]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=1N)([O-:3])=[O:2].N([O-])=O.[Na+].[BrH:18]>C(O)(=O)C.S(=O)(=O)(O)O.O.[Cu](Br)Br>[Br:18][C:5]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=1[N+:1]([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 260Hydrogen BromideHCID 136400Ar,ar-dinitrobenzenamineHCID 23668193Sodium Nitrite

Product 1

HCID 124898381-Bromo-2,3-dinitrobenzeneYield 99%

Reagents, catalysts & solvents 4

HCID 24611Copper bromide (CuBr2)CatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,3-dinitroaniline (2.27 g, 12.4 mmol) in 35 mL of glacial acetic acid was added dropwise to a stirred and cooled solution of sodium nitrite (0.95 g, 13.8 mmol) in concentrated sulfuric acid (7 mL) while the temperature of the reaction was held at 15-20° C. The resulting diazonium solution was then added over a five minute period to a stirred solution of copper bromide (1.85 g, 12.9 mmol) in a mixture of HBr (48%) (10 mL) and water (10 mL) heated at 75° C.-80° C. After the addition, the mixture was cooled to room temperature and added to water (500 mL). The light-green powder was filtered from the solution and dried in vacuum at room temperature to give the desired product 1-bromo-2,3-dinitrobenzene (3.0 g, 99%). This product was used in subsequent reaction without further purification. See, Donald L. Vivian J. Org. Chem. 1956, 21, 1188.

Workup

  1. customwas held at 15-20° C
  2. temperatureheated at 75° C.-80° C
  3. additionAfter the addition
  4. filtrationThe light-green powder was filtered from the solution
  5. customdried in vacuum at room temperature

Sources & evidence

ORD record
ord-432a568456814eb4849209757024a473
Source dataset
uspto-grants-2011_11
Patent number
US08063053B2

Reaction notes

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