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

HRID 369680Notes

Reaction equation

HRID 369680 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

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. additionwas added in portions
  2. stirringAfter stirring at room temperature for 1 hour
  3. distillationthe solvent was distilled out under reduced pressure
  4. dissolutionThe residue was dissolved in 300 ml of diethyl ether
  5. washwashed with 10% hydrochloric acid
  6. dry with materialwater, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Sources & evidence

ORD record
ord-13a86abe24ff4987a6dbdfcfa387d407
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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