2,4-Diisopropylphenol → 2-Bromo4,6-diisopropyl-phenol

HRID 1883222Notes

Reaction equation

HRID 1883222 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:13])([CH3:3])[CH3:2].[Br:14]Br>C(O)(=O)C>[Br:14][C:6]1[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[OH:13]

Participants

4

Reactant 2

HCID 180482,4-Diisopropylphenol2×HCID 24408Bromine

Product 1

HCID 145150292-Bromo4,6-diisopropyl-phenolYield 100.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-diisopropyl-phenol (Intermediate 1, 10.0 g, 56 mmol) in acetic acid (20 mL) was added bromine (3.5 mL, 67 mmol) at 0° C. The mixture was stirred at 0° C. for 15 min, quenched with water and extracted with EtOAc. The organic layer was washed successively with NaOH (4M, 85 mL), NaHSO3, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexanes) to yield the title compound as a light yellow oil (14.5 g, 100%).

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed successively with NaOH (4M, 85 mL), NaHSO3, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (hexanes)

Sources & evidence

ORD record
ord-40b8d677d3ff45379c297e1dbb08aba4
Source dataset
uspto-grants-2004_07
Patent number
US06759546B1

Reaction notes

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