2-Ethyl-6-methylphenol → 4-Bromo-2-ethyl-6-methylphenol

HRID 363095Notes

Reaction equation

HRID 363095 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[OH:10])[CH3:2].[Br-:11].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl>[Br:11][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([OH:10])=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

4

Reactant 2

HCID 5193332-Ethyl-6-methylphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 220068384-Bromo-2-ethyl-6-methylphenolYield 182.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Then, 16 g of 2-ethyl-6-methylphenol was dissolved in 200 ml of chloroform, followed by stirring at 0° C., to which 56.6 g of tetrabutylammonium tribromide was added in small portions. After stirring at room temperature for 1 hour, the solvent was removed by distillation under reduced pressure, and the residue was dissolved in 300 ml of diethyl ether. The solution was successively washed with 10% hydrochloric acid and water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 23 g of 4-bromo-2-ethyl-6-methylphenol (92% yield).

Workup

  1. additionwas added in small portions
  2. customthe solvent was removed by distillation under reduced pressure
  3. dissolutionthe residue was dissolved in 300 ml of diethyl ether
  4. washThe solution was successively washed with 10% hydrochloric acid and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain a crude product

Sources & evidence

ORD record
ord-12b1d64a1dd3461ba4f2a029abab3055
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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