2-Ethylphenol → 4-Bromo-2-ethylphenol

HRID 584294Notes

Reaction equation

HRID 584294 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].[Br-:10].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:10][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

5

Reactant 3

HCID 69972-EthylphenolHCID 24477Sodium ThiosulfateHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 878774-Bromo-2-ethylphenolYield 100.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.57 g (45 mmol) of 2-ethylphenol are placed in 250 ml of chloroform in a round-bottomed flask and under a stream of nitrogen. 43.4 g (90 mmol) of tetrabutylammonium tribromide are added portionwise. The medium is stirred for 1 hour at room temperature and is then hydrolysed with saturated aqueous sodium thiosulfate solution. The organic phase is washed with water, dried over magnesium sulfate, filtered and then evaporated. 9.1 g (100%) of the expected product are obtained in the form of a yellow oil.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f640c1f96cc744ada21ed968654e5f60
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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