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

HRID 264712Notes

Reaction equation

HRID 264712 reaction equation
[Br:1]Br.[CH:3]([C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[OH:15])([CH3:5])[CH3:4]>C(O)(=O)C.[Fe]>[CH:3]([C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([Br:1])[C:7]=1[OH:15])([CH3:5])[CH3:4]

Participants

5

Reactant 2

HCID 180482,4-DiisopropylphenolHCID 24408Bromine

Product 1

HCID 145150292-Bromo4,6-diisopropyl-phenolYield 85.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

1 g of iron powder and then, dropwise, 101 g (32.2 ml, 0.63 mol) of bromine are added in the course of 90 minutes to a solution of 102.3 g (0.57 mol) of 2,4-diisopropylphenol in 900 ml of glacial acetic acid at 95° C. The mixture is stirred for a further hour at 100° C. and cooled, the reaction mixture is partitioned between toluene and water and the toluene phase is washed with NaHCO3 solution. It is dried, filtered and concentrated, and the residue is distilled in a high vacuum. 125 g of the title compound is obtained as a pale yellow oil, b.p. 85° C./0.15 torr.

Workup

  1. temperaturecooled
  2. customthe reaction mixture is partitioned between toluene and water
  3. washthe toluene phase is washed with NaHCO3 solution
  4. customIt is dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationthe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-2efab375abcb4d3d937bf801377c3fed
Source dataset
uspto-grants-1997_07
Patent number
US05646272

Reaction notes

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