2-Ethylphenol → 4-Bromo-2-ethylphenol

HRID 859642Notes

Reaction equation

HRID 859642 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:55]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[OH:63])[CH3:56]>C(Cl)(Cl)Cl>[Br:1][C:61]1[CH:60]=[CH:59][C:58]([OH:63])=[C:57]([CH2:55][CH3:56])[CH:62]=1

Participants

4

Reactant 2

HCID 69972-EthylphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 878774-Bromo-2-ethylphenolYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of tetrabutyl ammonium tribromide (39.56 g, 0.08mol) in CHCl3 (100 mL) was added to a stirred solution of 2-ethyl-phenol (10.0 g, 0.08 mol) dissolved in CHCl3 (100 mL). The reaction mixture was stirred for 2 hrs and then quenched with 5% solution of sodium thiosulfate (100 mL). The biphasic mixture was stirred for 30 mins and then the layers were separated. The organic layer was washed with 1 N HCl, brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 15% EtOAc in hexanes) gave the product as an oil (14 g.). LCMS: APCI−VE=200 M/E.

Workup

  1. customquenched with 5% solution of sodium thiosulfate (100 mL)
  2. stirringThe biphasic mixture was stirred for 30 mins
  3. customthe layers were separated
  4. washThe organic layer was washed with 1 N HCl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a red oil
  7. customPurification by flash column chromatography (0% to 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1a1ef06a218e4d409708962e0c673268
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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