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

HRID 398068Notes

Reaction equation

HRID 398068 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>CC(O)=O>[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

4

Reactant 2

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

Product 1

HCID 5198222-Bromo-4,6-di-tert-butylphenolYield 91.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,4-di-t-butylphenol (Aldrich, 2.0 g, 9.7 mmol) in 2 ml of HOAc was added Br2 (0.5 ml, 9.7 mmol). The reaction mixture was stirred at room temperature for 12 hours. Solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate/hexane 1/20) to yield the desired product (2.54 g) as a white solid. 1H NMR δ7.33 (d, J=2.3 Hz, 1H), 7.24 (d, J=2.3 Hz, 1H), 1.41 (s, 9H), 1.29 (s, 9H).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (ethyl acetate/hexane 1/20)

Sources & evidence

ORD record
ord-e9321be272664a6289d41b9f2ad2a541
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

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