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

HRID 1417024Notes

Reaction equation

HRID 1417024 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-6a4b8f758e43454d94c5370068ebe609
Source dataset
uspto-grants-1999_06
Patent number
US05917048

Reaction notes

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