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

HRID 1727565Notes

Reaction equation

HRID 1727565 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-5d934faa509a44e4b55ef2e0dca89f81
Source dataset
uspto-grants-2009_02
Patent number
US07495103B2

Reaction notes

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