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

HRID 1844685Notes

Reaction equation

HRID 1844685 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].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[Br:12][C:9]1[CH:8]=[CH:7][C:6]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:10]=1

Participants

4

Reactant 2

HCID 69232-Tert-ButylphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 970684-Bromo-2-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-(tert-butyl)phenol (20 g, 133 mmol) in dry DCM (200 mL) was added tetrabutyl ammonium tribromide (64.3 g, 133 mmol) at 0° C. and the solution was stirred at rt for 2 h, concentrated and redissolved in Et2O, washed by brine (3×), dried over Na2SO4, filtered and concentrated to give compound P9a (36.6 g, 95%) as an oil.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in Et2O
  3. washwashed by brine (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give compound P9a (36.6 g, 95%) as an oil

Sources & evidence

ORD record
ord-9551418545354f128e41ddc49cde1b81
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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