Hydrogen Bromide → 4-bromo-2-tert-butylphenylamine

HRID 1698392Notes

Reaction equation

HRID 1698392 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[BrH:12].CS(C)=O.[OH-].[Na+]>C(O)(=O)C>[Br:12][C:10]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 805742-tert-Butylaniline

Product 1

HCID 119590004-bromo-2-tert-butylphenylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

25 g (168 mmol) of 2-tert-butylaniline are placed in 300 ml of acetic acid. 450 ml of aqueous HBr at 48% are added and the mixture is then cooled to 0° C. 150 ml of DMSO are added dropwise, the mixture having been brought back to ambient temperature is stirred for 2 hours and it is then poured into ice-cold water and basified to pH 10 with 5N NaOH. It is extracted with diethyl ether and the organic phase is then dried and concentrated to dryness. The residue is column-purified (95/5 heptane/EtOAc). 25.2 g of 4-bromo-2-tert-butylphenylamine are obtained in the form of a yellow oil (yield=65%).

Workup

  1. customhaving been brought back to ambient temperature
  2. extractionIt is extracted with diethyl ether
  3. customthe organic phase is then dried
  4. concentrationconcentrated to dryness
  5. customThe residue is column-purified (95/5 heptane/EtOAc)

Sources & evidence

ORD record
ord-6154685a0ef94d6fb61d5c4df54ac107
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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