Hydrochloric Acid → 1-Bromo-2,3,5-trichlorobenzene

HRID 1633468Notes

Reaction equation

HRID 1633468 reaction equation
N([O-])=O.[Na+].S(=O)(=O)(O)O.[Br:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[C:12]=1N.[ClH:20]>C(O)(=O)C>[Cl:20][C:12]1[C:14]([Cl:19])=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=1[Br:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 27569012-Bromo-4,6-dichloroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 43829031-Bromo-2,3,5-trichlorobenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium nitrite (3.88 g, 0.056 mole) was added in portions to concentrated sulphuric acid (28.16 ml) stirred below 10° C. A solution of 2-bromo-4,6-dichloroaniline (12 g, 0.05 mole, Lancaster) in glacial acetic acid (126 ml) was added maintaining the temperature below 10° C. The mixture was stirred below 10° C. for 1 hr and then slowly added to a stirred solution of cuprous chloride (10.11 g, 0.10 mole) in concentrated hydrochloric acid (101.05 ml) at room temperature. The mixture was then stirred at room temperature for 17 hrs. The product was filtered, washed with water (3×50 ml), dissolved in chloroform (150 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo to give the desired product. Yield 10 g (77%), M.p. 55-57° C.

Workup

  1. temperaturemaintaining the temperature below 10° C
  2. stirringThe mixture was stirred below 10° C. for 1 hr
  3. stirringThe mixture was then stirred at room temperature for 17 hrs
  4. filtrationThe product was filtered
  5. washwashed with water (3×50 ml)
  6. dissolutiondissolved in chloroform (150 ml)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-33c3c3b2f7484c569a8da42611404ba6
Source dataset
uspto-grants-2003_01
Patent number
US06503909B1

Reaction notes

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