Water → 2-Bromo-4,6-di-tert-butylphenol

HRID 1581465Notes

Reaction equation

HRID 1581465 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[Br:16]Br.O>C(O)(=O)C>[Br:16][C:7]1[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 73112,4-Di-tert-butylphenolHCID 24408Bromine

Product 1

HCID 5198222-Bromo-4,6-di-tert-butylphenolYield 72.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 150 ml of acetic acid, 20 g (96.9 millimole) of 2,4-di-tert-butylphenol was dissolved, and the solution was cooled on ice. Then, 5.0 ml (96.9 millimole) of bromine was added thereto drop by drop. After finishing dropwise addition, the temperature was elevated up to a room temperature, and the solution was stirred for 8 hours. Then, the reaction mixture was thrown into ice and water, and the aqueous layer was extracted with diethyl ether. The organic layer was dried on anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 19.96 g (yield: 72.0%) of 2-bromo-4, 6-di-tert-butylphenol.

Workup

  1. temperaturethe solution was cooled on ice
  2. additionaddition
  3. customwas elevated up to a room temperature
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1c9dc2cba287461bab5032141e2088e5
Source dataset
uspto-grants-2004_05
Patent number
US06730626B2

Reaction notes

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