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

HRID 2304781Notes

Reaction equation

HRID 2304781 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 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-7c1cf431c9ef427fb32f29426c4cdf0d
Source dataset
uspto-grants-2002_08
Patent number
US06437129B1

Reaction notes

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