Hydrogen Bromide → 1-Bromo-4-(2-methylbutan-2-yl)benzene

HRID 444430Notes

Reaction equation

HRID 444430 reaction equation
[BrH:1].[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH2:5][CH3:6])([CH3:4])[CH3:3].BrBr>[Fe].S(=O)(O)[O-].[Na+]>[Br:1][C:10]1[CH:9]=[CH:8][C:7]([C:2]([CH2:5][CH3:6])([CH3:3])[CH3:4])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 16295tert-AmylbenzeneHCID 24408Bromine

Product 1

HCID 129009891-Bromo-4-(2-methylbutan-2-yl)benzene

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 23665763Sodium BisulfiteSolvent

Conditions

Temperature
35 °C

Procedure

A glass reactor equipped with a mechanically driven stirrer, addition funnel and hydrogen bromide trap was charged with 300 g (2.02 mole) of t-amylbenzene and 8 g of iron filings. Bromine (374 g, 2.02 mole) was added dropwise at a rate such that the temperature of the reaction mixture was maintained at about 35° C. The reaction mixture was stirred for 15 hours while being heated to a temperature of 50° C. The contents of the reactor were then cooled and combined with 200 cc of a saturated aqueous sodium bisulfite solution. After being stirred for a few moments the reaction mixture was filtered. The organic layer was then separated and combined with a quantity of anhydrous magnesium sulfate to remove any water present. The liquid phase was then separated and distilled under a pressure of 0.1 mm of mercury. The fraction boiling from 70° to 75° C. was collected and analyzed for carbon, hydrogen and bromine.

Workup

  1. temperaturewhile being heated to a temperature of 50° C
  2. temperatureThe contents of the reactor were then cooled
  3. stirringAfter being stirred for a few moments the reaction mixture
  4. filtrationwas filtered
  5. customThe organic layer was then separated
  6. customto remove any water present
  7. customThe liquid phase was then separated
  8. distillationdistilled under a pressure of 0.1 mm of mercury
  9. customboiling from 70° to 75° C.
  10. customwas collected

Sources & evidence

ORD record
ord-f51315bd8d9e4cd784864e02ee88cf37
Source dataset
uspto-grants-1981_04
Patent number
US04264593

Reaction notes

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