Sulfuric Acid → 1,3-dibromo-5-nitrobenzene

HRID 1424560Notes

Reaction equation

HRID 1424560 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Br:12])[C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+]>C(O)C>[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Br:12])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 132312,6-Dibromo-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 2387111,3-dibromo-5-nitrobenzeneYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred, boiling (90° C.) mixture of 2,6-dibromo-4-nitroaniline (1 g, 3.38 mmol), ethanol (12 mL) and concentrated sulfuric acid (2 mL), sodium nitrite (0.75 g, 10.88 mmol) was added in portions as rapidly as foaming would permit. The reaction mixture was stirred at 90° C. for 30 h. The mixture was allowed to cool, poured into ice water and the solids were collected by filtration and washed with water. The 3,5-dibromobenzene was separated from the remaining inorganic salts by dissolving it in boiling ethanol and filtering the hot solution, from which 0.457 g (47% yield) of the product (30) crystallized on cooling: 1H-NMR (400 MHz, CDCl3) δ 8.32 (d, J=1.6 Hz, 2 H), 8.00 (t, J=1.6 Hz, 1 H).

Workup

  1. additionwas added in portions as rapidly as foaming
  2. temperatureto cool
  3. filtrationthe solids were collected by filtration
  4. washwashed with water
  5. customThe 3,5-dibromobenzene was separated from the remaining inorganic salts
  6. dissolutionby dissolving it
  7. filtrationfiltering the hot solution

Sources & evidence

ORD record
ord-e3726e8d76754c8784ec25ea772f27a3
Source dataset
uspto-grants-2015_01
Patent number
US08927728B2

Reaction notes

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