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

HRID 1739107Notes

Reaction equation

HRID 1739107 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>>[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

3

Reactant 2

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

Product 1

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

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 δ 7.33 (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-775d9c86a02543fcb04c5b0f5d1cfe94
Source dataset
uspto-grants-1999_10
Patent number
US05965606

Reaction notes

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