Diethyl Ether → 4-Bromo-2-tert-butylphenol

HRID 1295957Notes

Reaction equation

HRID 1295957 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])([CH3:12])([CH3:11])[CH3:10].CCOCC>C(#N)C>[Br:1][C:17]1[CH:16]=[CH:15][C:14]([OH:19])=[C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])[CH:18]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 69232-Tert-ButylphenolHCID 67184N-bromobutanimide

Product 1

HCID 970684-Bromo-2-tert-butylphenolYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (580 g) was gradually added to a solution of 2-(tert-butyl)phenol (489 g) in acetonitrile (4000 ml) while cooling on ice. After stirring for 4 hours at below 20° C., ether (3000 ml) was added and the reaction mixture was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to yield a crude product of the title compound (746 g) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. washthe reaction mixture was washed twice with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-54c5fc72b0f040678a843f9516a3842c
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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