2-Ethylphenol → 4-Bromo-2-ethylphenol

HRID 970830Notes

Reaction equation

HRID 970830 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-ethylphenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15 g (123 mmol) of 2-ethylphenol are dissolved in 150 ml of chloroform. 59 g (123 mmol) of tetrabutylammonium tribromide are added in portions of 10 g, and the reaction medium is stirred for 20 minutes. The medium is then poured into a saturated sodium thiosulphate solution, and then the pH is adjusted to 7. The mixture is extracted with dichloromethane. After drying and concentration, the residue obtained is purified by chromatography on a silica column (eluent ethyl acetate 10/heptane 90). A yellow oil is obtained (m=24.5 g, y=99%).

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. customAfter drying
  3. concentrationconcentration
  4. customthe residue obtained
  5. customis purified by chromatography on a silica column (eluent ethyl acetate 10/heptane 90)
  6. customA yellow oil is obtained (m=24.5 g, y=99%)

Sources & evidence

ORD record
ord-d375071df6c94bbb8f41133aaf0a6175
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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