2-Tert-Butylphenol → 4-Bromo-2-tert-butylphenol

HRID 2041971Notes

Reaction equation

HRID 2041971 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[Br:12]N1C(=O)CCC1=O>C(#N)C>[C:1]([C:5]1[CH:10]=[C:9]([Br:12])[CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 69232-Tert-ButylphenolHCID 67184N-bromobutanimide

Product 1

HCID 970684-Bromo-2-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-tert-butylphenol (25.0 g, 166.4 mmol) in acetonitrile (150 mL) was added N-bromosuccinimide (30.0 g, 168.5 mmol), and the mixture was stirred at room temperature for 16 hr. Petroleum ether (150 mL) was added to the reaction mixture, and the mixture was stirred at 0° C. for 1 hr. The precipitated white solid was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5-90:10) to give the title compound as a yellow oil. This was used for the next reaction without further purification.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hr
  2. filtrationThe precipitated white solid was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5-90:10)

Sources & evidence

ORD record
ord-cccd6b6e91ed49c9ad4d68e6c867c06e
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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