Bromine → 4-Bromo-2,6-diisopropylaniline

HRID 1446361Notes

Reaction equation

HRID 1446361 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[Br:14]Br>C(O)(=O)C>[Br:14][C:9]1[CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([NH2:6])=[C:7]([CH:11]([CH3:13])[CH3:12])[CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 32484Diisopropylaniline

Product 1

HCID 117801144-Bromo-2,6-diisopropylaniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 80.0 g (0.452 mol) of 2,6-diisopropylaniline in 2000 cm3 of glacial acetic acid, 23.3 ml (72.3 g, 0.452 mol) of bromine were added dropwise, while vigorously stirring, over 20 minutes. This mixture was stirred additionally for 2 hours at 40° C. The white precipitate that formed was filtered off, washed with 100 ml of acetic acid, and dried in air. The resulting white solid was added to a solution of 150 g of potassium hydroxide in 600 ml of water. This mixture was stirred for 30 minutes. The product was extracted with 3×100 ml of methyl-tert-butyl ether. The combined organic fractions were washed with Na2SO4 and evaporated to dryness. Fractional distillation gave a yellowish oil, b.p. 112-115° C./1 mm Hg. Yield 48.8 g (42%).

Workup

  1. stirringThis mixture was stirred additionally for 2 hours at 40° C
  2. customThe white precipitate that formed
  3. filtrationwas filtered off
  4. washwashed with 100 ml of acetic acid
  5. customdried in air
  6. additionThe resulting white solid was added to a solution of 150 g of potassium hydroxide in 600 ml of water
  7. stirringThis mixture was stirred for 30 minutes
  8. extractionThe product was extracted with 3×100 ml of methyl-tert-butyl ether
  9. washThe combined organic fractions were washed with Na2SO4
  10. customevaporated to dryness
  11. distillationFractional distillation
  12. customgave a yellowish oil, b.p. 112-115° C./1 mm Hg

Sources & evidence

ORD record
ord-a932905360a9448db6d50731358250e3
Source dataset
uspto-grants-2010_02
Patent number
US07667064B2

Reaction notes

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