2-Ethyl-5-methoxyphenol → 4-Bromo-5-methoxy-2-ethyl-phenol

HRID 859646Notes

Reaction equation

HRID 859646 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:55][O:56][C:57]1[CH:58]=[CH:59][C:60]([CH2:64][CH3:65])=[C:61]([OH:63])[CH:62]=1>C(Cl)(Cl)Cl>[Br:1][C:58]1[C:57]([O:56][CH3:55])=[CH:62][C:61]([OH:63])=[C:60]([CH2:64][CH3:65])[CH:59]=1

Participants

4

Reactant 2

HCID 125297512-Ethyl-5-methoxyphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 587640764-Bromo-5-methoxy-2-ethyl-phenolYield 104.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of tetrabutyl ammonium tribromide (38.10 g, 79 mmol) in CHCl3 (100 mL) was added to a stirred solution of 5-methoxy-2-ethyl-phenol (12.0 g, 79 mmol) dissolved in CHCl3 (90 mL). The reaction mixture was stirred for 4hrs and then quenched with 5% solution of sodium thiosulfate (90 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 60% EtOAc in hexanes) gave the product as an oil (19 g). LCMS : APCI−VE=230 M/E.

Workup

  1. customquenched with 5% solution of sodium thiosulfate (90 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 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-298edcffe41c44b1ab072d3d2d1f2448
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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