Sulfuric Acid → 1,3-dibromo-5-tert-butylbenzene

HRID 2071039Notes

Reaction equation

HRID 2071039 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[C:5]([Br:13])[C:3]=1N.OS(O)(=O)=O.N([O-])=O.[Na+].CCOC(C)=O>CCO.O>[Br:1][C:2]1[CH:8]=[C:7]([C:9]([CH3:11])([CH3:10])[CH3:12])[CH:6]=[C:5]([Br:13])[CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 27611662,6-dibromo-4-tert-butylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 27611701,3-dibromo-5-tert-butylbenzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of 2,6-dibromo-4-tert-butylaniline in 115 mL of EtOH was added 11.5 mL of concentrated H2SO4. To the stirring solution at 90° C. was added 8.8 g of NaNO2 in several portions. After 37 h, EtOAc and 120 mL of H2O were added, and the layers separated. The organic layer was washed with 40 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (hexanes) provided 8.15 g of 1,3-dibromo-5-tert-butylbenzene as a yellow-brown oil with some impurity.

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (hexanes)

Sources & evidence

ORD record
ord-8416306801ef44a9a6e83ed53358a32f
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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