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

HRID 401331Notes

Reaction equation

HRID 401331 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].C1C(=O)N([Br:19])C(=O)C1>CC#N>[C:1]([C:5]1[CH:10]=[C:9]([Br:19])[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-butylphenolYield 99.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-tert-butylphenol (250 g, 1.67 mol) in CH3CN (1500 mL) was added NBS (300 g, 1.67 mol) at room temperature. After addition, the mixture was stirred at room temperature overnight and then the solvent was removed. Petroleum ether (1000 mL) was added, and the resulting white precipitate was filtered off. The filtrate was concentrated under reduced pressure to give the crude 2-tert-butyl-4-bromophenol (380 g), which was used without further purification.

Workup

  1. additionAfter addition
  2. customthe solvent was removed
  3. additionPetroleum ether (1000 mL) was added
  4. filtrationthe resulting white precipitate was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-32b022589344474aa401038206309493
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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